Organic Chemistry Quiz Outline
Organic Chemistry Quiz Outline Table of Contents
Ch. 1 – Bonding, Resonance, and Molecular Geometry .................................................................. 1 Ch. 2 – Acids and Bases ....................................................................................................................... 7 Ch. 3 – Nomenclature ........................................................................................................................ 19 Ch. 4 – Stereochemistry ..................................................................................................................... 30 Ch. 5 – Spectroscopy .......................................................................................................................... 39 Ch. 6 – IM Forces and Lab Techniques ............................................................................................ 46 Ch. 7 – Reactions of Alkenes and Alkynes ....................................................................................... 52 Ch. 8 – Substitution and Elimination Reactions .............................................................................. 65 Ch. 9 – Free Radical Halogenation and Diels Alder ........................................................................ 72 Ch. 10 – Aromatic Compounds ......................................................................................................... 75 Ch. 11 – Alcohols, Ethers, Epoxides .................................................................................................. 80 Ch. 12 – Aldehydes and Ketones ...................................................................................................... 85 Ch. 13 – Carboxylic Acids and Acid Derivatives .............................................................................. 90 Ch. 14 – Alpha Substituion Reactions for Carbonyls ...................................................................... 94
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.1 – Molecular Bonding Geometry and Hybridization 1. What is the hybridization and bond angle of each atom indicated?
hybridization?
hybridization?
O
hybridization?
H
C C H
H
H
H
H
hybridization?
H
C
C
H
Quiz 1.2 – Condensed Formulas and Line-Bond Formulas 1. Write the condensed formula for each of the following structures:
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.3 – Sigma and Pi Bonds 1. How many sigma (σ) and pi (π) bonds are there in each of the molecules below?
Quiz 1.4 – Orbital Hybridization 1. In a C=C bond: A. Hybridization occurs between the s-orbital and one p-orbital B. Hybridization occurs between the s-orbital and two p-orbitals C. Hybridization occurs between the s-orbital and three p-orbital D. Hybridization occurs between the s- and one p-orbitals 2. π bonds are formed by which of the following orbitals? A. Two p-orbitals B. Two s-orbitals C. One s- and one p-orbital D. All of the above 3. How would one best describe the orbitals required to form a π bond? A. Parallel overlap of two s-orbitals B. Overlap of one s- and one p-orbital C. Perpendicular overlap of two p-orbitals D. Parallel overlap of two p-orbitals 4. How would one best describe the orbital required to form a σ bond? Select all that apply. A. Overlap of two s-orbitals B. Overlap of one s- and one p-orbital C. Overlap of two p-orbitals D. Parallel overlap of two p-orbitals
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.5 – Resonance Structures 1. Draw resonance contributors for each molecule below. Do not include structures that are so unstable that their contributions are negligible. For each molecule’s set of resonance contributors, indicate which is the greatest resonance contributor.
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.5 – Resonance Structures (Continued) 2. Which of the following structures represents a correct resonance structure for molecule A?
3. Draw resonance contributors for each radical molecule below. For each set of resonance contributors, indicate which is the greatest resonance contributor.
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.6 – Newman Projections 1. Which of the following represents the most stable Newman projection looking down the C2–C3 bond of 2-methylbutane?
2. Which of the following represents the most stable Newman projection looking down the C3–C2 bond of 2-methylbutane?
3. Which of the following represents the most stable conformation of 3,3-dimethylpentane viewed along the C3-C4 bond?
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.7 – Cycloalkanes and Ring Strain 1. Draw trans-1,2-dibromocyclohexane in a chair conformation.
2. Draw trans-1,2-dibromocyclohexane in its most stable chair conformation.
3. Which of the following represents the most stable chair conformation of the molecule shown in the box below?
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.1 – Acid-Base Definitions 1. The conjugate base of H3O+ is: A. B. C. D. E.
H3O– H2O H3O H3O+ HO–
2. What is the conjugate acid of C6H5NH2? A. B. C. D.
C6H5NH3+ C6H5NH– C6H5NH4+ C6H5NH2–
3. Which of the following is NOT a conjugate acid-base pair? A. B. C. D. E.
H2O, H3O+ Cl–, HCl SO42–, HSO4– NO3–, HNO3 – OH, O2–
4. Identify each substance in the following reactions as an acid, a base, a conjugate base, or a conjugate acid.
NH3 (aq) + HF (aq) → F– (aq) + NH4+ (aq)
NaOH (aq) + H2O (l) → NaOH (aq) + H2O (l)
KOH (aq) + H2CO3 (aq) → KHCO3 (aq) + H2O (l)
C2H3O2H (aq) + NaHCO3 (aq) → NaC2H3O2 (aq) + H2CO3 (aq)
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.2 – Conjugate Base-Acid Relationship and pH Scale 1. Which of the following is the weakest acid? A. B. C. D. E.
H2S (KA = 1.1 × 10-7) HCO2H (KA = 1.8 × 10-4) HF (KA = 6.8 × 10-4) NH4+ (KA = 5.6 × 10-10) Acetic acid (KA = 1.8 × 10-5)
2. Which of the following molecules would be the strongest acid?
OH
OH
O
3. Which of the following molecules would be the strongest acid?
4. Of the acids shown in the table below, __________ is the strongest acid. A. B. C. D. E.
C2H3OH H2C2O4 HClO2 HCO2H H2C6H6O6
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.2 – Conjugate Base-Acid Relationship and pH Scale (Continued) 5. Given the KA values in the table, which of the conjugate bases below is the strongest base? A. B. C. D. E.
C2H3O– HC2O4– ClO2– HCO2– HC6H6O6–
6. If H2O has a pKA of 15.7 and acetic acid has a pKA of 4.75, which is a stronger base, hydroxide (OH–) or acetate (C2H3O2–)?
7. Given the KB values in the table, which of the conjugate acids below is the weakest acid? A. B. C. D. E.
HCO2– C5H5NH+ NH4+ H3NOH+ H2S
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.3 – Ranking Acids and Bases with CARDIO (Charge) 1. Which of the red-colored H atoms below would be the most acidic?
2. Which of the red-colored H atoms below would be the most acidic?
3. Which of the red-colored H atoms below would be the most acidic?
4. Which of the red-colored H atoms below would be the most acidic? Which would be the least?
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.4 – Ranking Acids and Bases with CARDIO (Atom) 1. Which of the following is the strongest acid? A. B. C. D.
SeH2 GeH4 HBr AsH3
2. Which of the following would be the strongest acid? Which would be the weakest? A. B. C. D.
H2Se H2O H2Te H2S
3. Which of the following is the strongest acid? Which is the weakest? A. HF B. HBr C. H2O D. H2Se 4. Which of the following is the weakest acid? A. HCl B. H2O C. H3N D. H2Se 5. Which of the following is the most acidic? A. H2O B. CH4 C. H2S D. H2Se 6. Which of the following is the most basic? A. H3C– B. CH4 C. NH3 D. OH–
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.5 – Ranking Acids and Bases with CARDIO (Resonance) 1. Which of the following molecules is most acidic? Why?
2. Which of the red-colored hydrogen atoms in the molecules below is most acidic? Why?
3. Which of the labeled hydrogen atoms in the following structure is the most acidic?
4. Which of the labeled hydrogen atoms in the following structure is the most acidic?
Continue to next page…
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.5 – Ranking Acids and Bases with CARDIO (Resonance) (Continued) 5. Which of the labeled hydrogen atoms in the following structure is the most acidic?
6. The pKA of acetone is about 20. The pKA of propane is about 50. Why?
7. Which of the red-colored alpha-hydrogen atoms is the LEAST acidic?
8. Sort the compounds below in order of increasing acidity of their alpha-hydrogen atoms (colored red), from LEAST to MOST acidic:
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.6 – Ranking Acids and Bases with CARDIO (Dipole Induction) 1. Sort the following molecules from least to most acidic.
2. Sort the following molecules from least to most acidic.
3. Which of the following will be least acidic? Which will be the most acidic?
Continue to next page…
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.6 – Ranking Acids and Bases with CARDIO (Dipole Induction) (Continued) 4. Which of the following pairs does NOT correctly describe their relative acidities?
5. Sort the following molecules from least to most basic.
6. Which of the following would be a stronger base? Why?
7. Sort the following molecules from least to most basic.
8. Sort the following molecules from least to most nucleophilic.
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.7 – Ranking Acids and Bases with CARDIO (Orbitals) 1. Which of the red-colored hydrogen atoms below is most acidic?
2. Which of the red-colored hydrogen atoms below is most acidic? Which is the least?
3. Which of the red-colored hydrogen atoms below is most acidic?
4. Which of the red-colored hydrogen atoms below is most acidic?
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.8 – Acid and Base Review 1. Which of the options below is the conjugate acid of Molecule A?
2. Which of the following compounds is most acidic?
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.8 – Acid and Base Review (Continued) 3. Which of the indicated hydrogen atoms is most acidic?
4. Which of the following compounds is most acidic?
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.1 – IUPAC Basics and Naming Alkanes 1. Please give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.2 – Naming Cycloalkanes and Alkyl Halides 1. Give the names for each of the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.3 – Naming Alkenes 1. Name the following alkenes, including cis or trans designation:
2. Assign E or Z to the following compounds:
3. Name the following alkenes, including their correct E/Z designation:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.3 – Naming Alkenes (Continued) 4. Give the IUPAC names for the following compounds:
5. Which of these structures represents a trans (E) isomer?
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.3 – Naming Alkenes (Continued) 6. What is the IUPAC name for this compound:
7. Give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.4 – Naming Alcohols, Ethers, and Amines 8. Please give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.5 – Naming Aldehydes and Ketones 1. Please give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.6 – Naming Carboxylic Acids and Derivatives 1. Please give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.7 – Naming Aromatics 1. Please give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.8 – Naming Polyfunctional Compounds 1. Please give the IUPAC name for the following structures:
2. Which of the following are considered terminal functional groups? A. Ketones B. Carboxylic acids C. Aldehydes D. Both B and C 3. The IUPAC name for the structure shown below ends with what suffix?
A. B. C. D.
-ol -ide -al -oic acid
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.9 – Naming Spiro and Bicyclic Alkanes 1.
Please provide a correct IUPAC name for each of the following spiro alkanes:
2.
Please provide a correct IUPAC name for each of the following bicyclic alkanes:
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.1 – Isomers 1. Are the following molecules isomers of each other? If so, what kind?
Continue to next page…
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.1 – Isomers (Continued) 2. What are the following molecules? A. Structural isomers B. Enantiomers C. Diastereomers D. Identical compounds E. Meso compounds
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.2 – Chiral Centers 1. Please assign the correct R,S configuration to each of the following molecules:
HC CH2 CH3CH2
C CH3 H
2. Are each of the pairs of molecules shown below pairs of enantiomers?
3. Please assign the correct R,S configuration to each stereocenter in the following molecule:
H3C
CH2CH3 H
Br H
Br
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Please assign the correct IUPAC name to the following molecule, including the R,S designation.
H3C
CH2CH3 H
Br H
Br
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.3 – Diastereomers 1.
2.
3.
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.4 – Counting Stereoisomers 1. How many possible stereoisomers are there in the following molecule?
2. How many possible stereoisomers are there in the following molecule?
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.5 – Chirality and Physical Properties 1. Which of the following statements is true about a pair of enantiomers? A. They rotate plane-polarized light by exactly the same amount and in opposite directions. B. They rotate plane-polarized by differing amounts and in opposite directions. C. They rotate plane-polarized light by differing amounts and in the same direction. D. They have different melting points. E. They have the same melting point, but different boiling points. 2. Which of the following could be separated by physical means? A. Enantiomers B. Racemic mixtures C. Diastereomers D. Meso compounds E. None of the above 3. A 50/50 mixture two enantiomers is: A. Called a racemic mixture B. Optically inactive C. Meso D. Both A and B E. None of the above 4.
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.6 – Meso Compounds 1.
Quiz 4.7 – Fischer Projections 1. The molecule pictured in the box below is shown as a Fischer projection. Which of the following tetrahedral structures represents the same molecule?
Continue to next page…
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.7 – Fischer Projections (Continued) 2. Alanine, the amino acid pictured in the box below, is shown as a Fischer projection. Which of the following tetrahedral structures represents the same molecule?
3. Threose, the four-carbon sugar pictured in the box below, is shown as a Fischer projection. Which of the following line-bond structures represents the same molecule?
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.8 – D vs. L Sugars 1. Categorize each of the following as D or L molecules:
2. Is S-valine, shown below, a “D” or an “L” amino acid?
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.1 – IR Spectroscopy 1. IR spectroscopy is most useful for identifying: A. The stereochemistry of molecules B. A compound’s functional group C. Enantiomeric excess in a non-racemic mixture D. A compound’s purity 2. H2 doesn’t give an IR spectrum because: A. It isn’t possible to get an IR spectrum of a gas B. It has no atomic motions C. H2 doesn’t have a net dipole moment D. None of the above 3. The IR spectrum of an organic compound has no strong absorptions from 1600 to 2600 or any above 3000. What functional group is it likely to contain? A. Alcohol B. Aldehyde C. Amine D. ether 4. A strong infrared (IR) absorption band between 1750 and 1700 indicates which of the following functional groups?
5. Which of the following would give a strong IR absorption band at 1720 cm-1?
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.2 – UV Vis and Mass Spectrometry 1. UV spectroscopy is most useful for detecting: A. Cumulated dienes B. Carboxylic acids and amides C. Conjugated alkenes D. Esters 2. In mass spectrometry, peak abundances are measured relative to the: A. M peak B. Parent peak C. Smallest peak D. Largest peak 3. Mass spectrometry separates fragments according to: A. mass B. mass-to-charge ratio C. size D. shape 4. Which of these compounds would most likely show a base peak at m/z = 43?
5. The key fragment at m/z = 45 corresponds which of the following fragments?
6. A compound is analyzed by mass spectrometry. Its base peak at m/z = 81 comes from the most stable fragment. Which of the following is it?
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.3 – Degrees of Unsaturation 1. How many degrees of unsaturation does the following formula have: C3H6O?
2. How many degrees of unsaturation does the following formula have: C2H6O2?
3. How many degrees of unsaturation does the following formula have: C4H2O2?
4. How many degrees of unsaturation does the following formula have: C4H4O2?
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.4 – 13C-NMR Spectroscopy 1. How many different kinds of carbon atoms are there in the following molecules?
2. For each pair below, which of the two pink-colored carbon atoms in each pair is more positively charged (and hence, will appear further to the left by NMR)?
3. Predict what the 13C-NMR spectrum should look like for each of the following molecules:
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.5 – 1H-NMR Spectroscopy 1. How many different kinds of hydrogen atoms are there in the following molecules?
2. For each pair below, which of the sets of pink-colored hydrogen atoms in each pair is more positively-charged (and hence, will appear further to the left by NMR)?
3. Predict what the 1H-NMR spectrum should look like for each of the following molecules.
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.6 – Spectroscopy Analysis *Note: You likely will not see anything this hard on the DAT, but if you can answer these questions, you’ll be ready to answer anything spectroscopy related on the DAT. 1. Identify the compound that gives the following spectra. (Formula: C6H12O)
2. Identify the compound that gives the following spectra. (Formula: C6H12O2)
Continue on next page…
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.6 – Spectroscopy Analysis (Continued) 3. Identify the compound that gives the following spectra. (Formula: C5H12O)
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.1 – Intermolecular Forces 1. Can acetaldehyde (shown below) hydrogen-bond? What if we add water?
O H 2. What types of intermolecular forces does testosterone have? CH3 CH3 H
O
H
H H
O
3. Which pair of elements would form a bond with the greatest ionic character? A. B and Cl B. C and P C. Al and P D. Li and Cl E. N and F 4. Which of the following interactions gives ionic compounds their relatively high melting points? A. Hydrogen bonding B. London forces C. Ion-dipole forces D. Ion-ion attraction E. Dipole-dipole forces 5. Which of the following molecules will exhibit intermolecular hydrogen-bonding?
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.2 – Effect of IM Forces on Physical Properties 1. The following compounds all have similar molecular weights. Which compound would have the LOWEST boiling point?
2. The following compounds all have similar molecular weights. Which compound would have the LOWEST boiling point?
3. Which of the following would have the HIGHEST boiling point?
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.2 – Effect of IM Forces on Physical Properties (Continued) 4. Which is the following is TRUE? A. As vapor pressure decreases, boiling point decreases. B. As vapor pressure increases, boiling point increases. C. As vapor pressure increases, boiling point decreases. D. Vapor pressure increases with increasing molecular weight. E. Boiling point increases with decreasing molecular weight. 5. The following compounds all have similar molecular weights. Which compound would have the LOWEST melting point?
6. The following compounds all have similar molecular weights. Which compound would have the LOWEST melting point?
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.3 – Melting Points and Extractions 1. If partitioned (separated) between ether and water, which of the following molecules would show the greatest preference for the water layer?
Quiz 6.4 – Acid-Base Extractions 1. Which of the following would be the best way to separate a carboxylic acid from an amine? A. Extract the carboxylic acid into aqueous HCl B. Extract the amine into water C. Extract the carboxylic acid into aqueous NaOH D. Extract the carboxylic acid into water E. Extract the amine into aqueous NaOH 2. Which of the following would be the best way to separate a phenol from an amine? A. Extract the phenol into aqueous HCl B. Extract the amine into water C. Extract the phenol into water D. Extract the amine into aqueous NaOH E. Extract the phenol into aqueous NaOH 3. Which of the following would be the best way to separate a phenol from an amine? A. Extract the amine into water B. Extract the phenol into water C. Extract the amine into aqueous HCl D. Extract the amine into aqueous NaOH E. Extract the phenol into ether
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.5 – Distillation and Recrystallization 1. Which of the following is frequently used to separate volatile liquids with large differences in their boiling temperatures? A. Thin-layer chromatography B. Gas-liquid chromatography C. Sublimation D. Distillation E. Fractional distillation 2. Which of the following is frequently used to separate volatile liquids with moderate differences in their boiling temperatures? A. Thin-layer chromatography B. Gas-liquid chromatography C. Sublimation D. Distillation E. Fractional distillation 3. Which of the following is sometimes used to purify volatile solids? A. Thin-layer chromatography B. Gas-liquid chromatography C. Sublimation D. Distillation E. Fractional distillation 4. Which of the following is sometimes used to purify non-volatile solids? A. Thin-layer chromatography B. Gas-liquid chromatography C. Sublimation D. Distillation E. Recrystallization
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.6 – Chromatography 1. Which of the following can be used to separate non-volatile substances? A. Sublimation B. Distillation C. Gas-liquid chromatography D. Fractional distillation E. Thin-layer chromatography 2. Which of the following methods would MOST effectively separate two volatile compounds? A. Silica gel chromatography B. Thin layer chromatography C. Extraction D. Crystallization E. Gas-liquid chromatography
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.1 – Alkene Additions and Hydrohalogenations 1. Which is the most stable carbocation?
2. Which of the following is an intermediate in the Markovnikov addition of HBr to 1methylcyclohexene?
3. What is the major product of the following reaction?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.1 – Alkene Additions and Hydrohalogenations (Continued) 4. What is the major product of the following reaction?
Quiz 7.2 – Carbocation Rearrangements 1. Draw the major organic product generated by the following reaction:
2. What is the major product of the Markovknikov addition of HBr to the following molecule?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.3 – How to add –OH and –OR to Alkenes 1. Which of the following would produce a secondary alcohol when reacted with oxymercuration-demercuration conditions?
2. Which best describes the regioselectivity and stereospecificity in the oxymercurationdemercuration of an alkene? A. Markovnikov orientation with syn-addition B. Markovnikov orientation with anti-addition C. anti-Markovnikov orientation with syn-addition D. anti-Markovnikov orientation with anti-addition E. Markonikov orientation with both syn- and anti-addition 3. Which of the following reactions will lead to the formation of methoxycyclopentane as the major product?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.3 – How to add –OH and –OR to Alkenes (Continued) 4. Which set of reagents will accomplish the following transformation?
A. B. C. D. E.
BH3-THF, then H2O2/NaOH OsO4, t-BuOOH H3O+/CH3OH Hg(OAc)2/H2O, then NaBH4 m-CPBA, then NaOCH3
5. What is the major product of the following reaction?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.4 – Adding Halogens to Alkenes 1. What are the major products of the following reactions?
2. What is the major product of the following reaction?
3. What is the major product of the following reaction?
4. Challenge Question: Draw the product(s) of the following reaction:
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.5 – Anti-Markovnikov Alkene Additions 1. Predict the major organic product of the following reaction:
2. What compound is the expected product upon hydrohalogenation of 2-methylpent-2-ene with peroxide and HBr?
3. What is the major organic product of the following reaction?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.6 – Epoxides and Dihydroxylations 1. Which set of reagents will accomplish the following transformation?
A. B. C. D. E.
1. H2O2 1. (CH3)2S=CH2 1. Hg(OAc)2/NaOH, H2O2 1. OsO4 1. mCPBA
2. CH3OH 2. CH3O–Na+ 2. CH3Li 2. CH3MgBr 2. CH3MgBr
2. What are the major products of the following reactions?
3. Predict the major product of the following reaction:
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.6 – Epoxides and Dihydroxylations (Continued) 4. What reaction sequence is required to yield the product below?
A. B. C. D. E.
II → IV → III II → I IV → III III → IV II → IV → I
5. Which starting material gives the product in the reaction sequence below?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.7 – Ozonolysis 1. Please identify the missing reactant:
2. What is the structure of a compound, which has a molecular formula of C6H10, which upon ozonolysis and subsequent treatment with zinc and water, gives the following product?
Continue to next page…
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.7 – Ozonolysis (Continued) 3. What is the major organic product of the following reaction?
4. What is/are the product(s) of the following reaction?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.8 – Catalytic Hydrogenation 1. What are the products of the following reactions?
2. Which set of reagents will accomplish the following chemical transformation?
A. B. C. D. E.
(1) NaNH2, (2) CH3Br, (3) H3O+ H2, Lindlar Li, NH3 (1) LiAlH4, (2) H3O+ HgSO4, H2SO4
3. Which reagent is best for preparing (Z)-4-methyl-2-hexene from 4-methyl-2-hexyne? A. H2, Pd/C B. Na/NH3 C. H2NNH2, NaOH D. Zn(Hg) / HCl E. H2, Lindlar’s catalyst (Pd/CaCO3)
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.9 – Alkyne Addition Reactions 1. Predict the products of the following reactions:
2. Predict the products of the following reactions:
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.10 – Alkyne Hydration and Alkylation 1. Predict the products of the following reactions:
2. Predict the products of the following reactions:
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.1 – Substitution Reactions (Part 1) 1. In an SN2 reaction, what happens if you double the amount of the nucleophile or the electrophile? A. The rate will halve B. The rate will stay the same C. The rate will double D. The rate will triple E. The rate will quadruple 2. In an SN2 reaction, what happens if you double the amount of solvent? A. The rate will halve B. The rate will stay the same C. The rate will double D. The rate will triple E. The rate will be 1/4th 5. Which of the following is a feature of SN2 reactions? A. Their rate law is first-order B. They produce a stereochemical inversion of configuration. C. They have no rate-determining step. D. Solvent concentrations do not affect outcome. E. Steric factors do not influence the rate. 6. Which of the following will most readily undergo an SN2 reaction with NaOH?
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.1 – Substitution Reactions (Part 2) 1. Determine if each of the following substitution reactions will happen by an SN1 or SN2 mechanism. Then predict the products:
Br Li-I
Br
?
NaCN
?
O Br NaO
Cl
HS-
?
?
Continue to next page…
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.1 – Substitution Reactions (Part 2 Continued) 2. Determine if each of the following substitution reactions will happen by an SN1 or SN2 mechanism. Then predict the products: I NaCN ?
O
Br NaO
?
OTs H2O
?
heat Cl NaOH
?
O
I NaO
O
OH HO
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?
?
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.2 – Elimination Reactions 1. Determine if each of the following substitution reactions will happen by an E1 or E2 mechanism. Then predict the products:
2. Predict the major products of each of the following E2 reactions:
Continue to next page…
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.2 – Elimination Reactions (Continued) 3. Predict the major products of each of the following E1 reactions:
4. Predict the major products of each of the following elimination reactions:
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.3 – How to Choose between SN1, SN2, E1, E2 1. Predict the major products of the following reactions and identify them as SN1, SN2, E1, or E2: Br
KOH
CH3
Br CH3
CH3OH, heat
NaOH
Cl H3C CH3 CH3 OTs H3C
H2O, heat
CH3 CH3
CH3
CH3
HO
Br H3C
CH3 CH3
O Br
CH3
NaO H3C
CH3
CH3
CH3
CH3 I H3C
LiO
CH3 CH3
CH3 Continue to next page…
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.3 – How to Choose between SN1, SN2, E1, E2 (Continued) 2. Predict the major products of the following reactions and identify them as SN1, SN2, E1, or E2: I H3C
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NaCN CH3
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Ch. 9 – Free Radical Halogenation and Diels Alder
DAT Organic Chemistry Outline
Quiz 9.1 – Free Radical Halogenation 1. Show the major product(s) formed by reacting each of the following with Br2 and hv.
CH3
CH3
CH3
CH3 H3C
H3C CH3
H3C
CH3
CH3 CH3
H3C
CH3
H3C
CH3 CH3 CH3
2. Which of the following is an example of a free radical termination step?
3. Which of the following reactions represents a propagation step in the free radical bromination of propane?
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Ch. 9 – Free Radical Halogenation and Diels Alder
DAT Organic Chemistry Outline
Quiz 9.2 – NBS in Radical Halogenation 1. What will be the major product(s) of the reaction of 1-methylcyclohexene with EACH of the following reagents? 1. NBS/heat/peroxide 2. Br2/CH2Cl2 3. HBr 4. HBr/peroxide
Quiz 9.3 – Diels-Alder Reaction 1. Identify the diene and dienophile needed to assemble the following product by a DielsAlder reaction:
2. All of the following dienes would react in a Diels-Alder reaction EXCEPT for one. Which one is the EXCEPTION?
Continue to next page…
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Ch. 9 – Free Radical Halogenation and Diels Alder
DAT Organic Chemistry Outline
Quiz 9.3 – Diels-Alder Reaction (Continued) 3. What is the major organic product of the following reaction sequence?
4. What is the major product expected of the following Diels–Alder reaction? (Note: (+/–) refers to a racemic mixture)
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Ch. 10 – Aromatic Compounds
DAT Organic Chemistry Outline
Quiz 10.1 – How to Determine Aromaticity 1. Identify each of the following compounds as aromatic, non-aromatic, or anti-aromatic:
Quiz 10.2 – Effects of Aromaticity 1. Which of the following molecules will undergo an SN1 reaction more quickly? Why?
2. Which of the following molecules will be more acidic and why?
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Ch. 10 – Aromatic Compounds
DAT Organic Chemistry Outline
Quiz 10.3 – Side Reactions of Benzenes 1. Predict the products of the following reactions:
2 . Predict the products of the following reactions:
Continue to next page…
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Ch. 10 – Aromatic Compounds
DAT Organic Chemistry Outline
Quiz 10.3 – Side Reactions of Benzenes (Continued) 3. What is the final product of the following reaction?
4. What is the final product of the following reaction?
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Ch. 10 – Aromatic Compounds
DAT Organic Chemistry Outline
Quiz 10.4 – Electrophilic Aromatic Substitution (EAS) 1. What are the products of the following reactions?
2. The reaction of this molecule with Cl2 and AlCl3 will form:
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Ch. 10 – Aromatic Compounds
DAT Organic Chemistry Outline
Quiz 10.4 – Electrophilic Aromatic Substitution (EAS) (Continued) 3. What is/are the product(s) of the following reaction?
Quiz 10.5 – Diazonium Salts 1. What are the products of each of the following reaction sequences?
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Ch. 11 – Alcohols, Ethers, Epoxides
DAT Organic Chemistry Outline
Quiz 11.1 – Substitution and Elimination of Alcohols 1. Which best describes the mechanism of the reaction pictured?
A. B. C. D. E.
Free radical halogenation SN1 SN2 E1 E2
2. Which set of reagents will accomplish the following transformation in the highest yield?
A. B. C. D. E.
1. PBr3 1. NaI 1. NaH 1. H3O+ 1. H3O+
2. PhO–Na+ 2. Benzyl alcohol 2. Benzene 2. PhOH 2. PhMgBr
3. Rank the following leaving groups in increasing order of reactivity (i.e., from worst to best).
A. IV < I < III < V < II B. II < V < III < I < IV C. I < IV < III < II < V D. V < IV < I < III < II E. IV < III < I < II < V 4. What is the most likely mechanism by which this reaction occurs?
A. B. C. D.
SN1 SN2 E1 E2
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Ch. 11 – Alcohols, Ethers, Epoxides
DAT Organic Chemistry Outline
Quiz 11.1 – Substitution and Elimination of Alcohols (Continued) 5. Draw the mechanism and identify the major product of each reaction below:
Quiz 11.2 – Oxidizing Alcohols 1. What are the major products of the following reactions?
Continue to next page…
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Ch. 11 – Alcohols, Ethers, Epoxides
DAT Organic Chemistry Outline
Quiz 11.2 – Oxidizing Alcohols (Continued) 2. What are the major products of the following reactions?
3. What is the major organic product of the following reaction sequence?
4. Using multistep synthesis, how could you convert the following starting material into the indicated product?
5. What is the major product of the following reaction?
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Ch. 11 – Alcohols, Ethers, Epoxides
DAT Organic Chemistry Outline
Quiz 11.3 – Reactions of Ethers 1. What products would be formed by heating the following ethers with one equivalent of HCl?
2. What products would be formed by heating the following ethers with excess HCl?
Quiz 11.4 – Reactions of Epoxides 1. Draw the product(s) of the following reaction sequence:
1. Cl2, H2O 2. HO2. What are the major products of the following reactions?
O HCl CH3OH O CH3OCH3OH
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Ch. 11 – Alcohols, Ethers, Epoxides
DAT Organic Chemistry Outline
Quiz 11.4 – Reactions of Epoxides (Continued) 3. What reaction sequence is required to yield the product below?
A. B. C. D. E.
II → IV → III II → I IV → III III → IV II → IV → I
4. Predict the major product of the following reaction:
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Ch. 12 – Aldehydes and Ketones
DAT Organic Chemistry Outline
Quiz 12.1 – Alcohol Reactions with Carbonyls 1. Identify the product and draw the reaction mechanism for the following transformation: O
HO OH CH3
? acid
2. What are the organic products of the following reaction?
3. What product would you obtain if you reacted cyclohexanone with H+ and CH3CH2OH?
4. What product would you obtain if you reacted butanal with H+ and CH3OH?
5. How could you convert the reactant here into the product shown?
6. How could you convert the reactant here into the product shown?
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Ch. 12 – Aldehydes and Ketones
DAT Organic Chemistry Outline
Quiz 12.2 – Amine Reactions with Carbonyls 1. What is the product of the following reaction?
2. What is the product of the following reaction?
3. What is the product of the following reaction sequence?
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Ch. 12 – Aldehydes and Ketones
DAT Organic Chemistry Outline
Quiz 12.3 – Hydride Reductions 1. What is the major product of the following reaction?
2. How might you prepare the following alcohols from an aldehyde or ketone? OH
OH H
CH2CH2OH
Quiz 12.4 – Grignards and Organolithium Reactions with Carbonyls 1. What is the major organic product of the following reaction sequence?
Continue to next page…
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Ch. 12 – Aldehydes and Ketones
DAT Organic Chemistry Outline
Quiz 12.4 – Grignards and Organolithium Reactions with Carbonyls (Continued) 2. Which of the following compounds gives a secondary alcohol upon reaction with methylmagnesium bromide, followed by acid workup? A. butyl formate B. 2-butanone C. butanal D. methyl butanoate E. cyclopentanone 3. Use a Grignard reaction on an aldehyde or ketone to synthesize the following compounds: A. butan-2-ol B. 1-phenylpropan-2-ol C. 1-methylcyclohexanol D. diphenylethanol 4. Which set of reagents will accomplish the following transformation?
A. B. C. D. E.
cold dilute KMnO4, then PhCH2Br PDC, CH2Cl2, then PhOH Hg(OAc)2/NaOH, H2O2, then PhLi OsO4, then PhMgBr O3/(CH3)2S, then PhMgBr
Quiz 12.5 – Wittig Reaction 1. Identify the missing reagent: O
CH2 ?
A. B. C. D.
Ph3P+—CH2– CH2I2, Zn(Cu) 1. CH3MgBr; 2. H2O CH2=CH2, Ru catalyst
Continue to next page…
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Ch. 12 – Aldehydes and Ketones
DAT Organic Chemistry Outline
Quiz 12.5 – Wittig Reaction (Continued) 2. What is the major product of the following reaction?
Quiz 12.6 – Michael Additions (1,4-Addition) 1. Predict the major organic product of the following reaction.
2. The following compound was prepared by a conjugate addition reaction between an α,β -unsaturated ketone and an alcohol. Identify the two reactants: O
O
H3C
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Ch. 13 – Carboxylic Acids and Acid Derivatives
DAT Organic Chemistry Outline
Quiz 13.1 – Interconversion of Acid Derivatives 1. Which of the following reagents would accomplish the following transformation in highest yield?
2. Why doesn’t this reaction work?
3. What is the major organic product of the following reaction sequence?
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Ch. 13 – Carboxylic Acids and Acid Derivatives
DAT Organic Chemistry Outline
Quiz 13.2 – Physical Properties of Carboxylic Acids 1. How would you prepare each of the following products, starting from a Grignard reagent?
Quiz 13.3 – Fischer Esterification and Saponification 1. Predict the products of the following reactions:
2. What is the major organic product of the following reaction?
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Ch. 13 – Carboxylic Acids and Acid Derivatives
DAT Organic Chemistry Outline
Quiz 13.4 – Hydride Reductions of Acid Derivatives 1. Which of the following compounds provides butane-1,4-diol as one of the products when reacted with LiAlH4 in anhydrous diethyl ether?
A. I only B. II only C. III only D. I and II E. I and III
2. What is the major product of the following reaction?
3. Which set of reagents will accomplish the following transformation?
A. B. C. D. E.
liq. NH3 NaBH4, CH3OH PCC, CH2Cl2 LiAlH4, Et2O H2NNH2
Continue to next page…
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Ch. 13 – Carboxylic Acids and Acid Derivatives
DAT Organic Chemistry Outline
Quiz 13.4 – Hydride Reductions of Acid Derivatives (Continued) 4. All of the following statements regarding organometallic compounds are correct EXCEPT for one. Which one is the EXCEPTION? A. Grignard reagents add to the carbonyl group of aldehydes and ketones. B. Grignard reagents are decomposed in protic solvents. C. A Grignard reagent reacts as a negatively charged carbanion. D. Alkyllithium and Grignard reagents do not add to esters. E. Grignard reagents can be prepared in ether or tetrahydrofuran.
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Ch. 13 – Carboxylic Acids and Acid Derivatives
DAT Organic Chemistry Outline
Quiz 13.5 – Mild Hydride Reductions 1. Which of the following compounds is hydrolyzed most slowly with OH–?
2. What is the product of the following reaction sequence?
3. What is the product of the following reaction sequence?
4. What is the product of the following reaction sequence?
5. What is the product of the following reaction sequence?
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.1 – Alpha Substitution Reactions 1. Rank the indicated hydrogen atoms from LEAST acidic to MOST acidic.
A. A < B < C B. C < B < A C. C < A < B D. B < C < A E. B < A < C 2. Which statement regarding the following equilibrium is true?
A. B. C. D. E.
II is the conjugate base of III. Equilibrium favors I and II. I is 3 times more acidic than IV. I and III are resonance structures. II is the strongest base in this equilibrium system.
3. What is the major product of the following reaction?
4. What is the major organic product of the following reaction sequence?
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.2 – Alpha Halogenation and Haloform Reaction 1. What is/are the major product(s) of the following reaction?
2. Show how you could convert each of the following starting materials into the products indicated:
Continue to next page…
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.2 – Alpha Halogenation and Haloform Reaction (Continued) 3. 2-Acetylcyclohexanone is treated with excess D2O in catalytic base. How many deuterium atoms are expected to be exchanged with hydrogen atoms in this molecule? A. 2 B. 7 C. 3 D. 5 E. 6 4. Assuming that complete deuteration occurs, how many deuterium (D) atoms are incorporated into the following molecule?
A. B. C. D. E.
3 4 5 6 7
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.3 – Aldol Condensation 1. Which of the following compounds is the product of an Aldol addition reaction?
2. Predict the major organic product of the following reaction:
3. Show how to form the following products from an aldehyde or ketone, using an aldol condensation: A. 2-methyl-3-hydroxypentanal
B. 4,5-diethyl-5-hydroxy-3-octanone
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.4 – Claisen Condensation 1. Give the product of the following Claisen condensation reaction:
2. Give the product of the following Claisen condensation reaction:
3. Identify the starting material(s) and reaction conditions used to form the indicated product through a Claisen condenation:
4. Which of the following molecules would decarboxylate when heated? Why?
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.5 – Acetoacetic Ester Synthesis 1. How could you convert the given starting material into the product indicated?
2. How could you perform each of the following conversions? A. ethyl acetate --> butan-2-one
B. propanoic acid --> pentan-3-one
Quiz 14.6 – Malonic Ester Synthesis 1. How could you convert the given starting material into the product indicated?
2. How could you convert the given starting material into the product indicated?
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Ch. 1 – Bonding, Resonance, and Molecular Geometry .................................................................. 1 Ch. 2 – Acids and Bases ....................................................................................................................... 7 Ch. 3 – Nomenclature ........................................................................................................................ 19 Ch. 4 – Stereochemistry ..................................................................................................................... 30 Ch. 5 – Spectroscopy .......................................................................................................................... 39 Ch. 6 – IM Forces and Lab Techniques ............................................................................................ 46 Ch. 7 – Reactions of Alkenes and Alkynes ....................................................................................... 52 Ch. 8 – Substitution and Elimination Reactions .............................................................................. 65 Ch. 9 – Free Radical Halogenation and Diels Alder ........................................................................ 72 Ch. 10 – Aromatic Compounds ......................................................................................................... 75 Ch. 11 – Alcohols, Ethers, Epoxides .................................................................................................. 80 Ch. 12 – Aldehydes and Ketones ...................................................................................................... 85 Ch. 13 – Carboxylic Acids and Acid Derivatives .............................................................................. 90 Ch. 14 – Alpha Substituion Reactions for Carbonyls ...................................................................... 94
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.1 – Molecular Bonding Geometry and Hybridization 1. What is the hybridization and bond angle of each atom indicated?
hybridization?
hybridization?
O
hybridization?
H
C C H
H
H
H
H
hybridization?
H
C
C
H
Quiz 1.2 – Condensed Formulas and Line-Bond Formulas 1. Write the condensed formula for each of the following structures:
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.3 – Sigma and Pi Bonds 1. How many sigma (σ) and pi (π) bonds are there in each of the molecules below?
Quiz 1.4 – Orbital Hybridization 1. In a C=C bond: A. Hybridization occurs between the s-orbital and one p-orbital B. Hybridization occurs between the s-orbital and two p-orbitals C. Hybridization occurs between the s-orbital and three p-orbital D. Hybridization occurs between the s- and one p-orbitals 2. π bonds are formed by which of the following orbitals? A. Two p-orbitals B. Two s-orbitals C. One s- and one p-orbital D. All of the above 3. How would one best describe the orbitals required to form a π bond? A. Parallel overlap of two s-orbitals B. Overlap of one s- and one p-orbital C. Perpendicular overlap of two p-orbitals D. Parallel overlap of two p-orbitals 4. How would one best describe the orbital required to form a σ bond? Select all that apply. A. Overlap of two s-orbitals B. Overlap of one s- and one p-orbital C. Overlap of two p-orbitals D. Parallel overlap of two p-orbitals
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.5 – Resonance Structures 1. Draw resonance contributors for each molecule below. Do not include structures that are so unstable that their contributions are negligible. For each molecule’s set of resonance contributors, indicate which is the greatest resonance contributor.
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.5 – Resonance Structures (Continued) 2. Which of the following structures represents a correct resonance structure for molecule A?
3. Draw resonance contributors for each radical molecule below. For each set of resonance contributors, indicate which is the greatest resonance contributor.
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.6 – Newman Projections 1. Which of the following represents the most stable Newman projection looking down the C2–C3 bond of 2-methylbutane?
2. Which of the following represents the most stable Newman projection looking down the C3–C2 bond of 2-methylbutane?
3. Which of the following represents the most stable conformation of 3,3-dimethylpentane viewed along the C3-C4 bond?
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Ch. 1 – Bonding, Resonance, and Molecular Geometry
DAT Organic Chemistry Outline
Quiz 1.7 – Cycloalkanes and Ring Strain 1. Draw trans-1,2-dibromocyclohexane in a chair conformation.
2. Draw trans-1,2-dibromocyclohexane in its most stable chair conformation.
3. Which of the following represents the most stable chair conformation of the molecule shown in the box below?
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.1 – Acid-Base Definitions 1. The conjugate base of H3O+ is: A. B. C. D. E.
H3O– H2O H3O H3O+ HO–
2. What is the conjugate acid of C6H5NH2? A. B. C. D.
C6H5NH3+ C6H5NH– C6H5NH4+ C6H5NH2–
3. Which of the following is NOT a conjugate acid-base pair? A. B. C. D. E.
H2O, H3O+ Cl–, HCl SO42–, HSO4– NO3–, HNO3 – OH, O2–
4. Identify each substance in the following reactions as an acid, a base, a conjugate base, or a conjugate acid.
NH3 (aq) + HF (aq) → F– (aq) + NH4+ (aq)
NaOH (aq) + H2O (l) → NaOH (aq) + H2O (l)
KOH (aq) + H2CO3 (aq) → KHCO3 (aq) + H2O (l)
C2H3O2H (aq) + NaHCO3 (aq) → NaC2H3O2 (aq) + H2CO3 (aq)
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.2 – Conjugate Base-Acid Relationship and pH Scale 1. Which of the following is the weakest acid? A. B. C. D. E.
H2S (KA = 1.1 × 10-7) HCO2H (KA = 1.8 × 10-4) HF (KA = 6.8 × 10-4) NH4+ (KA = 5.6 × 10-10) Acetic acid (KA = 1.8 × 10-5)
2. Which of the following molecules would be the strongest acid?
OH
OH
O
3. Which of the following molecules would be the strongest acid?
4. Of the acids shown in the table below, __________ is the strongest acid. A. B. C. D. E.
C2H3OH H2C2O4 HClO2 HCO2H H2C6H6O6
Continue to next page…
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.2 – Conjugate Base-Acid Relationship and pH Scale (Continued) 5. Given the KA values in the table, which of the conjugate bases below is the strongest base? A. B. C. D. E.
C2H3O– HC2O4– ClO2– HCO2– HC6H6O6–
6. If H2O has a pKA of 15.7 and acetic acid has a pKA of 4.75, which is a stronger base, hydroxide (OH–) or acetate (C2H3O2–)?
7. Given the KB values in the table, which of the conjugate acids below is the weakest acid? A. B. C. D. E.
HCO2– C5H5NH+ NH4+ H3NOH+ H2S
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.3 – Ranking Acids and Bases with CARDIO (Charge) 1. Which of the red-colored H atoms below would be the most acidic?
2. Which of the red-colored H atoms below would be the most acidic?
3. Which of the red-colored H atoms below would be the most acidic?
4. Which of the red-colored H atoms below would be the most acidic? Which would be the least?
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.4 – Ranking Acids and Bases with CARDIO (Atom) 1. Which of the following is the strongest acid? A. B. C. D.
SeH2 GeH4 HBr AsH3
2. Which of the following would be the strongest acid? Which would be the weakest? A. B. C. D.
H2Se H2O H2Te H2S
3. Which of the following is the strongest acid? Which is the weakest? A. HF B. HBr C. H2O D. H2Se 4. Which of the following is the weakest acid? A. HCl B. H2O C. H3N D. H2Se 5. Which of the following is the most acidic? A. H2O B. CH4 C. H2S D. H2Se 6. Which of the following is the most basic? A. H3C– B. CH4 C. NH3 D. OH–
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.5 – Ranking Acids and Bases with CARDIO (Resonance) 1. Which of the following molecules is most acidic? Why?
2. Which of the red-colored hydrogen atoms in the molecules below is most acidic? Why?
3. Which of the labeled hydrogen atoms in the following structure is the most acidic?
4. Which of the labeled hydrogen atoms in the following structure is the most acidic?
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.5 – Ranking Acids and Bases with CARDIO (Resonance) (Continued) 5. Which of the labeled hydrogen atoms in the following structure is the most acidic?
6. The pKA of acetone is about 20. The pKA of propane is about 50. Why?
7. Which of the red-colored alpha-hydrogen atoms is the LEAST acidic?
8. Sort the compounds below in order of increasing acidity of their alpha-hydrogen atoms (colored red), from LEAST to MOST acidic:
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.6 – Ranking Acids and Bases with CARDIO (Dipole Induction) 1. Sort the following molecules from least to most acidic.
2. Sort the following molecules from least to most acidic.
3. Which of the following will be least acidic? Which will be the most acidic?
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.6 – Ranking Acids and Bases with CARDIO (Dipole Induction) (Continued) 4. Which of the following pairs does NOT correctly describe their relative acidities?
5. Sort the following molecules from least to most basic.
6. Which of the following would be a stronger base? Why?
7. Sort the following molecules from least to most basic.
8. Sort the following molecules from least to most nucleophilic.
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.7 – Ranking Acids and Bases with CARDIO (Orbitals) 1. Which of the red-colored hydrogen atoms below is most acidic?
2. Which of the red-colored hydrogen atoms below is most acidic? Which is the least?
3. Which of the red-colored hydrogen atoms below is most acidic?
4. Which of the red-colored hydrogen atoms below is most acidic?
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.8 – Acid and Base Review 1. Which of the options below is the conjugate acid of Molecule A?
2. Which of the following compounds is most acidic?
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Ch. 2 – Acids and Bases
DAT Organic Chemistry Outline
Quiz 2.8 – Acid and Base Review (Continued) 3. Which of the indicated hydrogen atoms is most acidic?
4. Which of the following compounds is most acidic?
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.1 – IUPAC Basics and Naming Alkanes 1. Please give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.2 – Naming Cycloalkanes and Alkyl Halides 1. Give the names for each of the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.3 – Naming Alkenes 1. Name the following alkenes, including cis or trans designation:
2. Assign E or Z to the following compounds:
3. Name the following alkenes, including their correct E/Z designation:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.3 – Naming Alkenes (Continued) 4. Give the IUPAC names for the following compounds:
5. Which of these structures represents a trans (E) isomer?
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.3 – Naming Alkenes (Continued) 6. What is the IUPAC name for this compound:
7. Give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.4 – Naming Alcohols, Ethers, and Amines 8. Please give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.5 – Naming Aldehydes and Ketones 1. Please give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.6 – Naming Carboxylic Acids and Derivatives 1. Please give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.7 – Naming Aromatics 1. Please give the IUPAC name for the following structures:
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.8 – Naming Polyfunctional Compounds 1. Please give the IUPAC name for the following structures:
2. Which of the following are considered terminal functional groups? A. Ketones B. Carboxylic acids C. Aldehydes D. Both B and C 3. The IUPAC name for the structure shown below ends with what suffix?
A. B. C. D.
-ol -ide -al -oic acid
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Ch. 3 – Nomenclature
DAT Organic Chemistry Outline
Quiz 3.9 – Naming Spiro and Bicyclic Alkanes 1.
Please provide a correct IUPAC name for each of the following spiro alkanes:
2.
Please provide a correct IUPAC name for each of the following bicyclic alkanes:
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.1 – Isomers 1. Are the following molecules isomers of each other? If so, what kind?
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.1 – Isomers (Continued) 2. What are the following molecules? A. Structural isomers B. Enantiomers C. Diastereomers D. Identical compounds E. Meso compounds
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.2 – Chiral Centers 1. Please assign the correct R,S configuration to each of the following molecules:
HC CH2 CH3CH2
C CH3 H
2. Are each of the pairs of molecules shown below pairs of enantiomers?
3. Please assign the correct R,S configuration to each stereocenter in the following molecule:
H3C
CH2CH3 H
Br H
Br
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Please assign the correct IUPAC name to the following molecule, including the R,S designation.
H3C
CH2CH3 H
Br H
Br
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.3 – Diastereomers 1.
2.
3.
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.4 – Counting Stereoisomers 1. How many possible stereoisomers are there in the following molecule?
2. How many possible stereoisomers are there in the following molecule?
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.5 – Chirality and Physical Properties 1. Which of the following statements is true about a pair of enantiomers? A. They rotate plane-polarized light by exactly the same amount and in opposite directions. B. They rotate plane-polarized by differing amounts and in opposite directions. C. They rotate plane-polarized light by differing amounts and in the same direction. D. They have different melting points. E. They have the same melting point, but different boiling points. 2. Which of the following could be separated by physical means? A. Enantiomers B. Racemic mixtures C. Diastereomers D. Meso compounds E. None of the above 3. A 50/50 mixture two enantiomers is: A. Called a racemic mixture B. Optically inactive C. Meso D. Both A and B E. None of the above 4.
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.6 – Meso Compounds 1.
Quiz 4.7 – Fischer Projections 1. The molecule pictured in the box below is shown as a Fischer projection. Which of the following tetrahedral structures represents the same molecule?
Continue to next page…
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.7 – Fischer Projections (Continued) 2. Alanine, the amino acid pictured in the box below, is shown as a Fischer projection. Which of the following tetrahedral structures represents the same molecule?
3. Threose, the four-carbon sugar pictured in the box below, is shown as a Fischer projection. Which of the following line-bond structures represents the same molecule?
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Ch. 4 – Stereochemistry
DAT Organic Chemistry Outline
Quiz 4.8 – D vs. L Sugars 1. Categorize each of the following as D or L molecules:
2. Is S-valine, shown below, a “D” or an “L” amino acid?
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.1 – IR Spectroscopy 1. IR spectroscopy is most useful for identifying: A. The stereochemistry of molecules B. A compound’s functional group C. Enantiomeric excess in a non-racemic mixture D. A compound’s purity 2. H2 doesn’t give an IR spectrum because: A. It isn’t possible to get an IR spectrum of a gas B. It has no atomic motions C. H2 doesn’t have a net dipole moment D. None of the above 3. The IR spectrum of an organic compound has no strong absorptions from 1600 to 2600 or any above 3000. What functional group is it likely to contain? A. Alcohol B. Aldehyde C. Amine D. ether 4. A strong infrared (IR) absorption band between 1750 and 1700 indicates which of the following functional groups?
5. Which of the following would give a strong IR absorption band at 1720 cm-1?
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.2 – UV Vis and Mass Spectrometry 1. UV spectroscopy is most useful for detecting: A. Cumulated dienes B. Carboxylic acids and amides C. Conjugated alkenes D. Esters 2. In mass spectrometry, peak abundances are measured relative to the: A. M peak B. Parent peak C. Smallest peak D. Largest peak 3. Mass spectrometry separates fragments according to: A. mass B. mass-to-charge ratio C. size D. shape 4. Which of these compounds would most likely show a base peak at m/z = 43?
5. The key fragment at m/z = 45 corresponds which of the following fragments?
6. A compound is analyzed by mass spectrometry. Its base peak at m/z = 81 comes from the most stable fragment. Which of the following is it?
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.3 – Degrees of Unsaturation 1. How many degrees of unsaturation does the following formula have: C3H6O?
2. How many degrees of unsaturation does the following formula have: C2H6O2?
3. How many degrees of unsaturation does the following formula have: C4H2O2?
4. How many degrees of unsaturation does the following formula have: C4H4O2?
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.4 – 13C-NMR Spectroscopy 1. How many different kinds of carbon atoms are there in the following molecules?
2. For each pair below, which of the two pink-colored carbon atoms in each pair is more positively charged (and hence, will appear further to the left by NMR)?
3. Predict what the 13C-NMR spectrum should look like for each of the following molecules:
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.5 – 1H-NMR Spectroscopy 1. How many different kinds of hydrogen atoms are there in the following molecules?
2. For each pair below, which of the sets of pink-colored hydrogen atoms in each pair is more positively-charged (and hence, will appear further to the left by NMR)?
3. Predict what the 1H-NMR spectrum should look like for each of the following molecules.
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.6 – Spectroscopy Analysis *Note: You likely will not see anything this hard on the DAT, but if you can answer these questions, you’ll be ready to answer anything spectroscopy related on the DAT. 1. Identify the compound that gives the following spectra. (Formula: C6H12O)
2. Identify the compound that gives the following spectra. (Formula: C6H12O2)
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Ch. 5 – Spectroscopy
DAT Organic Chemistry Outline
Quiz 5.6 – Spectroscopy Analysis (Continued) 3. Identify the compound that gives the following spectra. (Formula: C5H12O)
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.1 – Intermolecular Forces 1. Can acetaldehyde (shown below) hydrogen-bond? What if we add water?
O H 2. What types of intermolecular forces does testosterone have? CH3 CH3 H
O
H
H H
O
3. Which pair of elements would form a bond with the greatest ionic character? A. B and Cl B. C and P C. Al and P D. Li and Cl E. N and F 4. Which of the following interactions gives ionic compounds their relatively high melting points? A. Hydrogen bonding B. London forces C. Ion-dipole forces D. Ion-ion attraction E. Dipole-dipole forces 5. Which of the following molecules will exhibit intermolecular hydrogen-bonding?
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.2 – Effect of IM Forces on Physical Properties 1. The following compounds all have similar molecular weights. Which compound would have the LOWEST boiling point?
2. The following compounds all have similar molecular weights. Which compound would have the LOWEST boiling point?
3. Which of the following would have the HIGHEST boiling point?
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.2 – Effect of IM Forces on Physical Properties (Continued) 4. Which is the following is TRUE? A. As vapor pressure decreases, boiling point decreases. B. As vapor pressure increases, boiling point increases. C. As vapor pressure increases, boiling point decreases. D. Vapor pressure increases with increasing molecular weight. E. Boiling point increases with decreasing molecular weight. 5. The following compounds all have similar molecular weights. Which compound would have the LOWEST melting point?
6. The following compounds all have similar molecular weights. Which compound would have the LOWEST melting point?
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.3 – Melting Points and Extractions 1. If partitioned (separated) between ether and water, which of the following molecules would show the greatest preference for the water layer?
Quiz 6.4 – Acid-Base Extractions 1. Which of the following would be the best way to separate a carboxylic acid from an amine? A. Extract the carboxylic acid into aqueous HCl B. Extract the amine into water C. Extract the carboxylic acid into aqueous NaOH D. Extract the carboxylic acid into water E. Extract the amine into aqueous NaOH 2. Which of the following would be the best way to separate a phenol from an amine? A. Extract the phenol into aqueous HCl B. Extract the amine into water C. Extract the phenol into water D. Extract the amine into aqueous NaOH E. Extract the phenol into aqueous NaOH 3. Which of the following would be the best way to separate a phenol from an amine? A. Extract the amine into water B. Extract the phenol into water C. Extract the amine into aqueous HCl D. Extract the amine into aqueous NaOH E. Extract the phenol into ether
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.5 – Distillation and Recrystallization 1. Which of the following is frequently used to separate volatile liquids with large differences in their boiling temperatures? A. Thin-layer chromatography B. Gas-liquid chromatography C. Sublimation D. Distillation E. Fractional distillation 2. Which of the following is frequently used to separate volatile liquids with moderate differences in their boiling temperatures? A. Thin-layer chromatography B. Gas-liquid chromatography C. Sublimation D. Distillation E. Fractional distillation 3. Which of the following is sometimes used to purify volatile solids? A. Thin-layer chromatography B. Gas-liquid chromatography C. Sublimation D. Distillation E. Fractional distillation 4. Which of the following is sometimes used to purify non-volatile solids? A. Thin-layer chromatography B. Gas-liquid chromatography C. Sublimation D. Distillation E. Recrystallization
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Ch. 6 – IM Forces and Lab Techniques
DAT Organic Chemistry Outline
Quiz 6.6 – Chromatography 1. Which of the following can be used to separate non-volatile substances? A. Sublimation B. Distillation C. Gas-liquid chromatography D. Fractional distillation E. Thin-layer chromatography 2. Which of the following methods would MOST effectively separate two volatile compounds? A. Silica gel chromatography B. Thin layer chromatography C. Extraction D. Crystallization E. Gas-liquid chromatography
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.1 – Alkene Additions and Hydrohalogenations 1. Which is the most stable carbocation?
2. Which of the following is an intermediate in the Markovnikov addition of HBr to 1methylcyclohexene?
3. What is the major product of the following reaction?
Continue to next page…
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.1 – Alkene Additions and Hydrohalogenations (Continued) 4. What is the major product of the following reaction?
Quiz 7.2 – Carbocation Rearrangements 1. Draw the major organic product generated by the following reaction:
2. What is the major product of the Markovknikov addition of HBr to the following molecule?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.3 – How to add –OH and –OR to Alkenes 1. Which of the following would produce a secondary alcohol when reacted with oxymercuration-demercuration conditions?
2. Which best describes the regioselectivity and stereospecificity in the oxymercurationdemercuration of an alkene? A. Markovnikov orientation with syn-addition B. Markovnikov orientation with anti-addition C. anti-Markovnikov orientation with syn-addition D. anti-Markovnikov orientation with anti-addition E. Markonikov orientation with both syn- and anti-addition 3. Which of the following reactions will lead to the formation of methoxycyclopentane as the major product?
Continue to next page…
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.3 – How to add –OH and –OR to Alkenes (Continued) 4. Which set of reagents will accomplish the following transformation?
A. B. C. D. E.
BH3-THF, then H2O2/NaOH OsO4, t-BuOOH H3O+/CH3OH Hg(OAc)2/H2O, then NaBH4 m-CPBA, then NaOCH3
5. What is the major product of the following reaction?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.4 – Adding Halogens to Alkenes 1. What are the major products of the following reactions?
2. What is the major product of the following reaction?
3. What is the major product of the following reaction?
4. Challenge Question: Draw the product(s) of the following reaction:
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.5 – Anti-Markovnikov Alkene Additions 1. Predict the major organic product of the following reaction:
2. What compound is the expected product upon hydrohalogenation of 2-methylpent-2-ene with peroxide and HBr?
3. What is the major organic product of the following reaction?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.6 – Epoxides and Dihydroxylations 1. Which set of reagents will accomplish the following transformation?
A. B. C. D. E.
1. H2O2 1. (CH3)2S=CH2 1. Hg(OAc)2/NaOH, H2O2 1. OsO4 1. mCPBA
2. CH3OH 2. CH3O–Na+ 2. CH3Li 2. CH3MgBr 2. CH3MgBr
2. What are the major products of the following reactions?
3. Predict the major product of the following reaction:
Continue to next page…
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.6 – Epoxides and Dihydroxylations (Continued) 4. What reaction sequence is required to yield the product below?
A. B. C. D. E.
II → IV → III II → I IV → III III → IV II → IV → I
5. Which starting material gives the product in the reaction sequence below?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.7 – Ozonolysis 1. Please identify the missing reactant:
2. What is the structure of a compound, which has a molecular formula of C6H10, which upon ozonolysis and subsequent treatment with zinc and water, gives the following product?
Continue to next page…
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.7 – Ozonolysis (Continued) 3. What is the major organic product of the following reaction?
4. What is/are the product(s) of the following reaction?
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.8 – Catalytic Hydrogenation 1. What are the products of the following reactions?
2. Which set of reagents will accomplish the following chemical transformation?
A. B. C. D. E.
(1) NaNH2, (2) CH3Br, (3) H3O+ H2, Lindlar Li, NH3 (1) LiAlH4, (2) H3O+ HgSO4, H2SO4
3. Which reagent is best for preparing (Z)-4-methyl-2-hexene from 4-methyl-2-hexyne? A. H2, Pd/C B. Na/NH3 C. H2NNH2, NaOH D. Zn(Hg) / HCl E. H2, Lindlar’s catalyst (Pd/CaCO3)
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.9 – Alkyne Addition Reactions 1. Predict the products of the following reactions:
2. Predict the products of the following reactions:
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Ch. 7 – Alkenes and Alkynes
DAT Organic Chemistry Outline
Quiz 7.10 – Alkyne Hydration and Alkylation 1. Predict the products of the following reactions:
2. Predict the products of the following reactions:
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.1 – Substitution Reactions (Part 1) 1. In an SN2 reaction, what happens if you double the amount of the nucleophile or the electrophile? A. The rate will halve B. The rate will stay the same C. The rate will double D. The rate will triple E. The rate will quadruple 2. In an SN2 reaction, what happens if you double the amount of solvent? A. The rate will halve B. The rate will stay the same C. The rate will double D. The rate will triple E. The rate will be 1/4th 5. Which of the following is a feature of SN2 reactions? A. Their rate law is first-order B. They produce a stereochemical inversion of configuration. C. They have no rate-determining step. D. Solvent concentrations do not affect outcome. E. Steric factors do not influence the rate. 6. Which of the following will most readily undergo an SN2 reaction with NaOH?
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.1 – Substitution Reactions (Part 2) 1. Determine if each of the following substitution reactions will happen by an SN1 or SN2 mechanism. Then predict the products:
Br Li-I
Br
?
NaCN
?
O Br NaO
Cl
HS-
?
?
Continue to next page…
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.1 – Substitution Reactions (Part 2 Continued) 2. Determine if each of the following substitution reactions will happen by an SN1 or SN2 mechanism. Then predict the products: I NaCN ?
O
Br NaO
?
OTs H2O
?
heat Cl NaOH
?
O
I NaO
O
OH HO
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?
?
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.2 – Elimination Reactions 1. Determine if each of the following substitution reactions will happen by an E1 or E2 mechanism. Then predict the products:
2. Predict the major products of each of the following E2 reactions:
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.2 – Elimination Reactions (Continued) 3. Predict the major products of each of the following E1 reactions:
4. Predict the major products of each of the following elimination reactions:
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.3 – How to Choose between SN1, SN2, E1, E2 1. Predict the major products of the following reactions and identify them as SN1, SN2, E1, or E2: Br
KOH
CH3
Br CH3
CH3OH, heat
NaOH
Cl H3C CH3 CH3 OTs H3C
H2O, heat
CH3 CH3
CH3
CH3
HO
Br H3C
CH3 CH3
O Br
CH3
NaO H3C
CH3
CH3
CH3
CH3 I H3C
LiO
CH3 CH3
CH3 Continue to next page…
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Ch. 8 – Substitution and Elimination Reactions
DAT Organic Chemistry Outline
Quiz 8.3 – How to Choose between SN1, SN2, E1, E2 (Continued) 2. Predict the major products of the following reactions and identify them as SN1, SN2, E1, or E2: I H3C
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NaCN CH3
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Ch. 9 – Free Radical Halogenation and Diels Alder
DAT Organic Chemistry Outline
Quiz 9.1 – Free Radical Halogenation 1. Show the major product(s) formed by reacting each of the following with Br2 and hv.
CH3
CH3
CH3
CH3 H3C
H3C CH3
H3C
CH3
CH3 CH3
H3C
CH3
H3C
CH3 CH3 CH3
2. Which of the following is an example of a free radical termination step?
3. Which of the following reactions represents a propagation step in the free radical bromination of propane?
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Ch. 9 – Free Radical Halogenation and Diels Alder
DAT Organic Chemistry Outline
Quiz 9.2 – NBS in Radical Halogenation 1. What will be the major product(s) of the reaction of 1-methylcyclohexene with EACH of the following reagents? 1. NBS/heat/peroxide 2. Br2/CH2Cl2 3. HBr 4. HBr/peroxide
Quiz 9.3 – Diels-Alder Reaction 1. Identify the diene and dienophile needed to assemble the following product by a DielsAlder reaction:
2. All of the following dienes would react in a Diels-Alder reaction EXCEPT for one. Which one is the EXCEPTION?
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Ch. 9 – Free Radical Halogenation and Diels Alder
DAT Organic Chemistry Outline
Quiz 9.3 – Diels-Alder Reaction (Continued) 3. What is the major organic product of the following reaction sequence?
4. What is the major product expected of the following Diels–Alder reaction? (Note: (+/–) refers to a racemic mixture)
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Ch. 10 – Aromatic Compounds
DAT Organic Chemistry Outline
Quiz 10.1 – How to Determine Aromaticity 1. Identify each of the following compounds as aromatic, non-aromatic, or anti-aromatic:
Quiz 10.2 – Effects of Aromaticity 1. Which of the following molecules will undergo an SN1 reaction more quickly? Why?
2. Which of the following molecules will be more acidic and why?
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Ch. 10 – Aromatic Compounds
DAT Organic Chemistry Outline
Quiz 10.3 – Side Reactions of Benzenes 1. Predict the products of the following reactions:
2 . Predict the products of the following reactions:
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Ch. 10 – Aromatic Compounds
DAT Organic Chemistry Outline
Quiz 10.3 – Side Reactions of Benzenes (Continued) 3. What is the final product of the following reaction?
4. What is the final product of the following reaction?
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Ch. 10 – Aromatic Compounds
DAT Organic Chemistry Outline
Quiz 10.4 – Electrophilic Aromatic Substitution (EAS) 1. What are the products of the following reactions?
2. The reaction of this molecule with Cl2 and AlCl3 will form:
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Ch. 10 – Aromatic Compounds
DAT Organic Chemistry Outline
Quiz 10.4 – Electrophilic Aromatic Substitution (EAS) (Continued) 3. What is/are the product(s) of the following reaction?
Quiz 10.5 – Diazonium Salts 1. What are the products of each of the following reaction sequences?
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Ch. 11 – Alcohols, Ethers, Epoxides
DAT Organic Chemistry Outline
Quiz 11.1 – Substitution and Elimination of Alcohols 1. Which best describes the mechanism of the reaction pictured?
A. B. C. D. E.
Free radical halogenation SN1 SN2 E1 E2
2. Which set of reagents will accomplish the following transformation in the highest yield?
A. B. C. D. E.
1. PBr3 1. NaI 1. NaH 1. H3O+ 1. H3O+
2. PhO–Na+ 2. Benzyl alcohol 2. Benzene 2. PhOH 2. PhMgBr
3. Rank the following leaving groups in increasing order of reactivity (i.e., from worst to best).
A. IV < I < III < V < II B. II < V < III < I < IV C. I < IV < III < II < V D. V < IV < I < III < II E. IV < III < I < II < V 4. What is the most likely mechanism by which this reaction occurs?
A. B. C. D.
SN1 SN2 E1 E2
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Ch. 11 – Alcohols, Ethers, Epoxides
DAT Organic Chemistry Outline
Quiz 11.1 – Substitution and Elimination of Alcohols (Continued) 5. Draw the mechanism and identify the major product of each reaction below:
Quiz 11.2 – Oxidizing Alcohols 1. What are the major products of the following reactions?
Continue to next page…
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Ch. 11 – Alcohols, Ethers, Epoxides
DAT Organic Chemistry Outline
Quiz 11.2 – Oxidizing Alcohols (Continued) 2. What are the major products of the following reactions?
3. What is the major organic product of the following reaction sequence?
4. Using multistep synthesis, how could you convert the following starting material into the indicated product?
5. What is the major product of the following reaction?
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Ch. 11 – Alcohols, Ethers, Epoxides
DAT Organic Chemistry Outline
Quiz 11.3 – Reactions of Ethers 1. What products would be formed by heating the following ethers with one equivalent of HCl?
2. What products would be formed by heating the following ethers with excess HCl?
Quiz 11.4 – Reactions of Epoxides 1. Draw the product(s) of the following reaction sequence:
1. Cl2, H2O 2. HO2. What are the major products of the following reactions?
O HCl CH3OH O CH3OCH3OH
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Ch. 11 – Alcohols, Ethers, Epoxides
DAT Organic Chemistry Outline
Quiz 11.4 – Reactions of Epoxides (Continued) 3. What reaction sequence is required to yield the product below?
A. B. C. D. E.
II → IV → III II → I IV → III III → IV II → IV → I
4. Predict the major product of the following reaction:
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Ch. 12 – Aldehydes and Ketones
DAT Organic Chemistry Outline
Quiz 12.1 – Alcohol Reactions with Carbonyls 1. Identify the product and draw the reaction mechanism for the following transformation: O
HO OH CH3
? acid
2. What are the organic products of the following reaction?
3. What product would you obtain if you reacted cyclohexanone with H+ and CH3CH2OH?
4. What product would you obtain if you reacted butanal with H+ and CH3OH?
5. How could you convert the reactant here into the product shown?
6. How could you convert the reactant here into the product shown?
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Ch. 12 – Aldehydes and Ketones
DAT Organic Chemistry Outline
Quiz 12.2 – Amine Reactions with Carbonyls 1. What is the product of the following reaction?
2. What is the product of the following reaction?
3. What is the product of the following reaction sequence?
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Ch. 12 – Aldehydes and Ketones
DAT Organic Chemistry Outline
Quiz 12.3 – Hydride Reductions 1. What is the major product of the following reaction?
2. How might you prepare the following alcohols from an aldehyde or ketone? OH
OH H
CH2CH2OH
Quiz 12.4 – Grignards and Organolithium Reactions with Carbonyls 1. What is the major organic product of the following reaction sequence?
Continue to next page…
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Ch. 12 – Aldehydes and Ketones
DAT Organic Chemistry Outline
Quiz 12.4 – Grignards and Organolithium Reactions with Carbonyls (Continued) 2. Which of the following compounds gives a secondary alcohol upon reaction with methylmagnesium bromide, followed by acid workup? A. butyl formate B. 2-butanone C. butanal D. methyl butanoate E. cyclopentanone 3. Use a Grignard reaction on an aldehyde or ketone to synthesize the following compounds: A. butan-2-ol B. 1-phenylpropan-2-ol C. 1-methylcyclohexanol D. diphenylethanol 4. Which set of reagents will accomplish the following transformation?
A. B. C. D. E.
cold dilute KMnO4, then PhCH2Br PDC, CH2Cl2, then PhOH Hg(OAc)2/NaOH, H2O2, then PhLi OsO4, then PhMgBr O3/(CH3)2S, then PhMgBr
Quiz 12.5 – Wittig Reaction 1. Identify the missing reagent: O
CH2 ?
A. B. C. D.
Ph3P+—CH2– CH2I2, Zn(Cu) 1. CH3MgBr; 2. H2O CH2=CH2, Ru catalyst
Continue to next page…
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Ch. 12 – Aldehydes and Ketones
DAT Organic Chemistry Outline
Quiz 12.5 – Wittig Reaction (Continued) 2. What is the major product of the following reaction?
Quiz 12.6 – Michael Additions (1,4-Addition) 1. Predict the major organic product of the following reaction.
2. The following compound was prepared by a conjugate addition reaction between an α,β -unsaturated ketone and an alcohol. Identify the two reactants: O
O
H3C
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Ch. 13 – Carboxylic Acids and Acid Derivatives
DAT Organic Chemistry Outline
Quiz 13.1 – Interconversion of Acid Derivatives 1. Which of the following reagents would accomplish the following transformation in highest yield?
2. Why doesn’t this reaction work?
3. What is the major organic product of the following reaction sequence?
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Ch. 13 – Carboxylic Acids and Acid Derivatives
DAT Organic Chemistry Outline
Quiz 13.2 – Physical Properties of Carboxylic Acids 1. How would you prepare each of the following products, starting from a Grignard reagent?
Quiz 13.3 – Fischer Esterification and Saponification 1. Predict the products of the following reactions:
2. What is the major organic product of the following reaction?
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Ch. 13 – Carboxylic Acids and Acid Derivatives
DAT Organic Chemistry Outline
Quiz 13.4 – Hydride Reductions of Acid Derivatives 1. Which of the following compounds provides butane-1,4-diol as one of the products when reacted with LiAlH4 in anhydrous diethyl ether?
A. I only B. II only C. III only D. I and II E. I and III
2. What is the major product of the following reaction?
3. Which set of reagents will accomplish the following transformation?
A. B. C. D. E.
liq. NH3 NaBH4, CH3OH PCC, CH2Cl2 LiAlH4, Et2O H2NNH2
Continue to next page…
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Ch. 13 – Carboxylic Acids and Acid Derivatives
DAT Organic Chemistry Outline
Quiz 13.4 – Hydride Reductions of Acid Derivatives (Continued) 4. All of the following statements regarding organometallic compounds are correct EXCEPT for one. Which one is the EXCEPTION? A. Grignard reagents add to the carbonyl group of aldehydes and ketones. B. Grignard reagents are decomposed in protic solvents. C. A Grignard reagent reacts as a negatively charged carbanion. D. Alkyllithium and Grignard reagents do not add to esters. E. Grignard reagents can be prepared in ether or tetrahydrofuran.
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Ch. 13 – Carboxylic Acids and Acid Derivatives
DAT Organic Chemistry Outline
Quiz 13.5 – Mild Hydride Reductions 1. Which of the following compounds is hydrolyzed most slowly with OH–?
2. What is the product of the following reaction sequence?
3. What is the product of the following reaction sequence?
4. What is the product of the following reaction sequence?
5. What is the product of the following reaction sequence?
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.1 – Alpha Substitution Reactions 1. Rank the indicated hydrogen atoms from LEAST acidic to MOST acidic.
A. A < B < C B. C < B < A C. C < A < B D. B < C < A E. B < A < C 2. Which statement regarding the following equilibrium is true?
A. B. C. D. E.
II is the conjugate base of III. Equilibrium favors I and II. I is 3 times more acidic than IV. I and III are resonance structures. II is the strongest base in this equilibrium system.
3. What is the major product of the following reaction?
4. What is the major organic product of the following reaction sequence?
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.2 – Alpha Halogenation and Haloform Reaction 1. What is/are the major product(s) of the following reaction?
2. Show how you could convert each of the following starting materials into the products indicated:
Continue to next page…
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.2 – Alpha Halogenation and Haloform Reaction (Continued) 3. 2-Acetylcyclohexanone is treated with excess D2O in catalytic base. How many deuterium atoms are expected to be exchanged with hydrogen atoms in this molecule? A. 2 B. 7 C. 3 D. 5 E. 6 4. Assuming that complete deuteration occurs, how many deuterium (D) atoms are incorporated into the following molecule?
A. B. C. D. E.
3 4 5 6 7
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.3 – Aldol Condensation 1. Which of the following compounds is the product of an Aldol addition reaction?
2. Predict the major organic product of the following reaction:
3. Show how to form the following products from an aldehyde or ketone, using an aldol condensation: A. 2-methyl-3-hydroxypentanal
B. 4,5-diethyl-5-hydroxy-3-octanone
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.4 – Claisen Condensation 1. Give the product of the following Claisen condensation reaction:
2. Give the product of the following Claisen condensation reaction:
3. Identify the starting material(s) and reaction conditions used to form the indicated product through a Claisen condenation:
4. Which of the following molecules would decarboxylate when heated? Why?
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Ch. 14 – Alpha Substitution Reactions of Carbonyls
DAT Organic Chemistry Outline
Quiz 14.5 – Acetoacetic Ester Synthesis 1. How could you convert the given starting material into the product indicated?
2. How could you perform each of the following conversions? A. ethyl acetate --> butan-2-one
B. propanoic acid --> pentan-3-one
Quiz 14.6 – Malonic Ester Synthesis 1. How could you convert the given starting material into the product indicated?
2. How could you convert the given starting material into the product indicated?
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