Base Equilibrium
FUNCTIONAL GROUPS AND IUPAC NAMING Wize Organic Chemistry Lecture Series, 2017 Presented by: Spencer
FUNCTIONAL GROUPS AND IUPAC T E ACH I NG OB J E CT I VES
1. Functional Groups 2. IUPAC Naming 3. Review Questions
FUNCTIONAL GROUPS Alkene Oxidation State
Alkyne Oxidation State Carboxylic Acid Oxidation State
FUNCTIONAL GROUPS Circle and name the functional groups present in the following molecules:
IUPAC NAMING Step 1: Identify the longest alkyl chain (find the backbone)
Find the longest carbon backbone of the following compounds. How many carbons?
IUPAC NAMING Step 2: Choose the appropriate carbon chain prefix
# of Carbons
Prefix
# of Carbons
Prefix
# of Carbons
Prefix
1
Meth-
5
Pent-
9
Non-
2
Eth-
6
Hex-
10
Dec-
3
Prop-
7
Hept-
11
Undec-
4
But-
8
Oct-
12
Dodec-
IUPAC NAMING Step 3: If present, assign stereochemistry (i.e. R/S and E/Z)
IUPAC NAMING Step 4: Assign priorities to the functional groups and determine chain numbering
Key Idea Functional Group Priorities Halide < Alkane < Alkyne < Alkene < Amine < Thiol < Alcohol < Ketone < Aldehyde < Nitrile < Amide < Acid Chloride < Ester < Carboxylic Acid
IUPAC NAMING Step 5: If necessary, give prefixes to the lowest priority functional groups Group
Suffix
Halogen
Bromo, Chloro…
Alkane
Methyl, ethyl...
Ketone
Oxo-
Aldehyde
formyl-
Alcohol
hydroxy-
Thiol
mercapto-
Amine
amino-
Nitrile
cyano-
IUPAC NAMING Step 6: Name the compound using the appropriate numbering and suffix Group
Suffix
Alkane
-ane
Alkene
-ene
Alkyne
-yne
Ketone
-one
Aldehyde
-al
Carb. Acid
-oic Acid
Ester
-oate
Alcohol
-ol
Thiol
-thiol
Amine
-amine
Key Idea: Order of functional groups is based on priority
IUPAC NAMING REVIEW
Step 1: Identify the longest alkyl chain (find the backbone) Step 2: Choose the appropriate carbon chain prefix Step 3: If present, assign stereochemistry (i.e. R/S and E/Z) Step 4: Assign priorities to the functional groups and determine chain numbering
Step 5: If necessary, give prefixes to the lowest priority functional groups Step 6: Name the compound using the appropriate numbering and suffix
FUNCTIONAL GROUPS AND IUPAC REVIEW
Circle and name all the functional groups (excluding alkanes) in the following molecules:
FUNCTIONAL GROUPS AND IUPAC REVIEW
Provide an IUPAC name for each of the following compounds:
FUNCTIONAL GROUPS AND IUPAC REVIEW
Provide a structure for each of the following compounds:
(E)-3-methylhex-3-en-2-one (2R,3S)-3-fluorobutan-2-ol (R)-3-methylpent-4-ynal
Methyl Pentanoate
FUNCTIONAL GROUPS AND IUPAC T E ACH I NG OB J E CT I VES
1. Functional Groups 2. IUPAC Naming 3. Review Questions
FUNCTIONAL GROUPS Alkene Oxidation State
Alkyne Oxidation State Carboxylic Acid Oxidation State
FUNCTIONAL GROUPS Circle and name the functional groups present in the following molecules:
IUPAC NAMING Step 1: Identify the longest alkyl chain (find the backbone)
Find the longest carbon backbone of the following compounds. How many carbons?
IUPAC NAMING Step 2: Choose the appropriate carbon chain prefix
# of Carbons
Prefix
# of Carbons
Prefix
# of Carbons
Prefix
1
Meth-
5
Pent-
9
Non-
2
Eth-
6
Hex-
10
Dec-
3
Prop-
7
Hept-
11
Undec-
4
But-
8
Oct-
12
Dodec-
IUPAC NAMING Step 3: If present, assign stereochemistry (i.e. R/S and E/Z)
IUPAC NAMING Step 4: Assign priorities to the functional groups and determine chain numbering
Key Idea Functional Group Priorities Halide < Alkane < Alkyne < Alkene < Amine < Thiol < Alcohol < Ketone < Aldehyde < Nitrile < Amide < Acid Chloride < Ester < Carboxylic Acid
IUPAC NAMING Step 5: If necessary, give prefixes to the lowest priority functional groups Group
Suffix
Halogen
Bromo, Chloro…
Alkane
Methyl, ethyl...
Ketone
Oxo-
Aldehyde
formyl-
Alcohol
hydroxy-
Thiol
mercapto-
Amine
amino-
Nitrile
cyano-
IUPAC NAMING Step 6: Name the compound using the appropriate numbering and suffix Group
Suffix
Alkane
-ane
Alkene
-ene
Alkyne
-yne
Ketone
-one
Aldehyde
-al
Carb. Acid
-oic Acid
Ester
-oate
Alcohol
-ol
Thiol
-thiol
Amine
-amine
Key Idea: Order of functional groups is based on priority
IUPAC NAMING REVIEW
Step 1: Identify the longest alkyl chain (find the backbone) Step 2: Choose the appropriate carbon chain prefix Step 3: If present, assign stereochemistry (i.e. R/S and E/Z) Step 4: Assign priorities to the functional groups and determine chain numbering
Step 5: If necessary, give prefixes to the lowest priority functional groups Step 6: Name the compound using the appropriate numbering and suffix
FUNCTIONAL GROUPS AND IUPAC REVIEW
Circle and name all the functional groups (excluding alkanes) in the following molecules:
FUNCTIONAL GROUPS AND IUPAC REVIEW
Provide an IUPAC name for each of the following compounds:
FUNCTIONAL GROUPS AND IUPAC REVIEW
Provide a structure for each of the following compounds:
(E)-3-methylhex-3-en-2-one (2R,3S)-3-fluorobutan-2-ol (R)-3-methylpent-4-ynal
Methyl Pentanoate
