Organic II Exam #3 Ch 20-21 (100 points). NAME: 1) Name the ...
Organic II Exam #3
Ch 20-21
(100 points).
NAME:
1)
Name the general class of organic compounds that each of these molecules belong to, and for the amides indicate whether they are primary, secondary or tertiary. (13pts)
R N
O R C F
R C R
O R C NR2
O R C O-R
R C N
O O R C O C R
O R C NH2
O R C OH
O O NH O
Org II Exam 3
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2)
Circle the stronger acid in the following pairs, and in a sentence explain your choice. (6pts)
CO2H
(a)
(b)
3)
(a)
(b)
CFH2CH2 CO2H
CO2H
CH3CClH CO2H
Circle the stronger base in the following pairs, and in a sentence explain your choice. (9pts)
CH3CH2 NH2
H H3C C N C CH3 O
(c)
O2N
CH3
H H3C C N CH 3
O
CH3CH2 NH2
O NH C CH3
O
CH3 C N
Org II Exam 3
Page 2
4) Name the following compounds in IUPAC acceptable terms. (20pts) O
F O
O
O
O
O
NH
NH2 O
OH
H2N O
Org II Exam 3
Page 3
5) Fill in all the missing products or reagents, and draw the mechanism for one of the reactions below. (16pts) O C
OH Ph C CH2CH3 CH3CH2
O Ph C Cl
O Ph C O
O C
Org II Exam 3
CH3CH2OH
CH3
Page 4
6) Fill in all the missing products or reagents, and draw the mechanism for one of the reactions below. (16pts)
H2O H2SO4 heat POCl3
Br2, KOH O Ph C NH2
H2 C NH2 Ph
Org II Exam 3
Page 5
6) Give the products for the following transformations.(8pts) O
O C
O
C
C
O
NH3, H3O+
O
NH3, H3O+
7) Draw the mechanism for one of the above reactions, and indicate which reaction you would predict to occur the quickest. (12pts)
Org II Exam 3
Page 6
*Bonus question* (up to 4pts) Write the mechanism for the below Curtius rearrangement, that involves the conversion of an acid chloride to an isocyanate. (Hint: its mechanistically identical to the Hofmann rearrangement). O R C Cl
O _ + N R C N N
Org II Exam 3
R N C O
Page 7
Ch 20-21
(100 points).
NAME:
1)
Name the general class of organic compounds that each of these molecules belong to, and for the amides indicate whether they are primary, secondary or tertiary. (13pts)
R N
O R C F
R C R
O R C NR2
O R C O-R
R C N
O O R C O C R
O R C NH2
O R C OH
O O NH O
Org II Exam 3
Page 1
2)
Circle the stronger acid in the following pairs, and in a sentence explain your choice. (6pts)
CO2H
(a)
(b)
3)
(a)
(b)
CFH2CH2 CO2H
CO2H
CH3CClH CO2H
Circle the stronger base in the following pairs, and in a sentence explain your choice. (9pts)
CH3CH2 NH2
H H3C C N C CH3 O
(c)
O2N
CH3
H H3C C N CH 3
O
CH3CH2 NH2
O NH C CH3
O
CH3 C N
Org II Exam 3
Page 2
4) Name the following compounds in IUPAC acceptable terms. (20pts) O
F O
O
O
O
O
NH
NH2 O
OH
H2N O
Org II Exam 3
Page 3
5) Fill in all the missing products or reagents, and draw the mechanism for one of the reactions below. (16pts) O C
OH Ph C CH2CH3 CH3CH2
O Ph C Cl
O Ph C O
O C
Org II Exam 3
CH3CH2OH
CH3
Page 4
6) Fill in all the missing products or reagents, and draw the mechanism for one of the reactions below. (16pts)
H2O H2SO4 heat POCl3
Br2, KOH O Ph C NH2
H2 C NH2 Ph
Org II Exam 3
Page 5
6) Give the products for the following transformations.(8pts) O
O C
O
C
C
O
NH3, H3O+
O
NH3, H3O+
7) Draw the mechanism for one of the above reactions, and indicate which reaction you would predict to occur the quickest. (12pts)
Org II Exam 3
Page 6
*Bonus question* (up to 4pts) Write the mechanism for the below Curtius rearrangement, that involves the conversion of an acid chloride to an isocyanate. (Hint: its mechanistically identical to the Hofmann rearrangement). O R C Cl
O _ + N R C N N
Org II Exam 3
R N C O
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