1.)
2.)
3.)
4.)
5.)
6.)
7.)
8.)
9.)
10.)
What is the best choice of reagents to perform the following
transformation?
OH
O
H3C
H3C
CH3
O
O
a.) CH3OH, H2SO4
11.)
b.) CH3I, H2SO4
c.) NaOCH3
d.) CH3Li
Rank the following compounds in order of decreasing acidity
(most acidic  least acidic).
O
O
O
F
H3C
OH
OH
F
F
II
I
a.) I>II>III
12.)
OH
b.) II>III>I
III
c.) III>I>II
d.) III>II>I
Which method would not be an acceptable synthesis of the following
compound?
O
O
a.)
b.)
c.)
d.)
CH3
Benzoic acid + methanol + acid catalyst
Benzoyl chloride + methanol
Benzoic anhydride + methanol + acid catalyst
Benzanamide + methanol + acid catalyst
13.)
Which of the following is a correct order of activity towards ethanol?
a.)
b.)
c.)
d.)
14.)
Anhydride > Ester > Acid Chloride
Ester > Amide > Anhydride
Acid Chloride > Ester > Anhydride
Acid Chloride > Anhydride > Ester
Rank the following benzoic acids in order of increasing acidity
(least acidic  most acidic).
COOH
F
H3C
3
2
1
a.)
b.)
c.)
d.)
e.)
COOH
COOH
3<2<1
2<1<3
2<3<1
1<2<3
1<3<2
15.) Reactions of aldehydes and ketones are classified as
reactions of carboxylic acid derivatives are classified as
a.)
b.)
c.)
d.)
while
.
elimination : nucleophilic substitution
nucleophilic substitution : nucleophilic addition
nucleophilic addition : elimination
nucleophilic addition : nucleophilic substitution
16.) Which of the following has the highest boiling point?
a.) pentane
b.) 1-pentanol
c.) 2-pentanol
d.) pentanoic acid
17.) Name the following compound.
O
H3C
OH
H3C
a.) E-4-ethyl-3-pentenoic acid
b.) E-4-methyl-3-hexenoic acid
c.) Z-4-ethyl-3-pentenoic acid
d.) Z-4-methyl-3-hexenoic acid
18.) Choose the correct starting material for the following conversion.
?
CH 3OH
a.) anhydride
RCOOCH 3
b.) acid chloride
c.) amide
d.) a and b
19.) Which of the following would decarboxylate the fastest?
O
O
O
H3C
H3C
OH
a.)
OH
O
c.)
O
O
O
O
OH
H3C
b.)
OH
d.)
CH3
20.) Which of the following is a lactam?
O
O
H3C
NH2
a.)
c.)
NH
O
d.) H3C
O
b.)
O
O
Short Answer
1.)
2.) Complete the following synthesis. Show all reagents, reaction conditions, and
intermediate compounds.
O
OH
NH2
CH3
CH3
CH3
3.) Provide the structures for compounds A  E below.
CH3
Br
KCN
A
DMSO
H3O
HO
+
B
H2 O
SOCl 2
CH3
C
NH 3
D
CHCl 3
pyridine
ether
4.) Explain why amides are less basic and less nucleophilic than amines. Explain
why imides are more acidic than amides.
5.) Explain why two moles of nitrogen compound are needed when synthesizing
an amide from and acid chloride or an acid anhydride and why this is not the
case for an ester.
6.) Explain why two moles of Grignard reagent are needed when synthesizing an
alcohol from an acid chloride or an ester but not when synthesizing an alcohol
from an aldehyde or ketone.
7.) Explain the trend that is observed in carboxylic acid derivative reactivity.
8.) Classify each of the products below, determine what reaction was used to synthesize each
product, and show the mechanism for the formation of each.
O
O
O
O
a.)
CH3
HO
CH3
H3C
b.)
CH3
O
H3C
c.)
O
d.) H3C
O
O
CH3
E
9.) Determine the products of the following reaction. Label the products as 1,2 or 1,4 and as
thermodynamic or kinetic and explain your choices. Show the complete mechanism.
CH2
HBr
H2C
CH3
10.) Provide the products or reagents for the following reactions.
O
H3C
1.) LiAlH 4,ether
OH
2.) H 3O
O
OH
O
+
H3C
O
O
OH
O
CH3
O
1.) NaBH 4,ethanol
2.) H 3O
CH3
O
+
+
CH3
K2Cr2O7
H3C
OH
H3O
+
NH2
N
O
CH3
O
H3C
H3C
O
H
CH3
H3C
O
O
H3C
CH3
OH
H3C
H
O
H3C
O
OH
CH3
H3O
+
H2O
O
O
NH2
O
H3C
H3C
CH3
O
O
CH3
Cl
H3C
H3C
H3C
O
OH
NH2 1.) LiAlH 4,ether
H3C
2.) H 3O
O
+
NH2
Cl
H3C
H3C
O
O
O
H3 O
H3C
+
NH2
H2O
Br
H3C
1.) NaCN
2.) H 3O/H2O
O
HNO 3
heat
O
OH
1.) BH 3,THF
2.) H 2O
O
O
2 CH 3CH 2NH 2
H3C
O
CH3
O
H3C
O
O
CH3
CH3
H3C
CH3CH2OH
O
H3C
NH
CH3
NH
CH3
1.) LiAlH 4, ether
N
H3C
CH3
O
2.) H 3O
+
O
CH3
H3C
H2 O
OH
-
O
O
H2O
H3C
NH2
H3C
CH3
H
OH
-
hot, conc., KMnO 4
H3O
CH3
HC
CH3
O3
or
+
KMnO 4
H3O
O
H3C
+
1.) 2 CH3CH2CH2Li,ether
OH
2.) H3O
+
O
OH
heat
HO
O
O
O
Cl
H3C
OH
+
H3C
O
H3C
NH2
SOCl 2
N 1.) CH3CH2CH2CH2MgBr, ether
H3C
2.) H3O
+