Chapter 19.

Aldehydes and
Ketones: Nucleophilic
Addition Reactions
醛 與 酮 : 親核加成反應
 Which of the following will not
19.1 produce an aldehyde or a ketone ?
O
1. °C
1) DIBAH, toluene, -78 ÞC
OCH3
2) H3O+

2. OH PCC

CH2Cl2

3. H3O+

HgSO4

4. 1) O3

2) Zn, CH3CO2H
19.1 answer
O
1. 1) DIBAH, toluene, -78 ÞC
°C
OCH3
2) H3O+

2. OH PCC

CH2Cl2

3. H3O+

HgSO4

4. 1) O3

2) Zn, CH3CO2H
19.2 O
HCN
C
CH3CH2 H

CN
OH (b)
(a)
CN OH

COOH
(c) (d) CN

OH
O
19.2 answer

CN
OH (b)
(a)
CN OH

Cyanohydrin

COOH
(c) (d) CN

OH
O
 O
19.3 H2NOH
CH2 C
H3C CH2 H H+

OH
(a)
NH (b) OH
N
H

(c)
(d)
OH NH2
N N
19.3 answer O 1o amine Derivative

H2NOH
CH2 C
H3C CH2 H H+

OH
(a)
NH (b) OH
N
H

(c)
(d)
OH NH2
N N

Imine Derivative
19.4 Which represents the product of this reaction?
O Ph2NH

H+

1. 2.
Ph
N Ph Ph 3.
N Ph
NH

4. 5.
Ph Ph NH2
N
19.4 answer
O Ph2NH 2o amine

H+

1. 2. 3.
Ph Ph
N Ph Ph NH
N

4.
Ph
N
Ph 5.
NH2

enamine
19.5 O
1. NH2NH2
H3C C
CH2 CH3 -
2. OH, heat

NNH2
NHNH2
(a) (b)

NH (d)
(c)
19.5 answer Wolff–Kishner Reduction

NNH2
NHNH2
(a) (b)

NH (d)
(c)

An intermediate hydrazone is formed,

which is then reduced to an alkane.
 O
19.6 2 CH3CH2OH
C
H3C CH3 H+

(a) H3CH2CO OH (b)

HO OH

(c)

H3CH2CO OCH2CH3
19.6 answer

(a) H3CH2CO OH (b)

HO OH

(c)

H3CH2CO OCH2CH3

Acetal
19.7
Which of the following represents an acetal?
1. 2.
O OCH3 HO OCH3
H

3.
O

OH

4.
O 5.
HO OH

OCH3
19.7 answer

1. 2.
O OCH3 HO OCH3
H

3.
O

OH

4.
O 5.
HO OH

OCH3
 O
19.8
Ph3P CH(CH3)2
C
CH 3CH2 H

(a) (b)

OH

(c) (d)
 19.8 answer Wittig Reaction

(a) (b)

OH
(c) (d)

The C(CH3)2 group replaces the oxygen

on the aldehyde.
Level 3
Challenging
 Which combination of reagents will yield the
19.9 following compound?
Ph

Ph
1. 2.
O O
+ PPh3 PPh3
Ph H +
Ph
Ph

3.
O
4.
+ PPh3 Both (1) and (2)
Ph Ph

5.
Both (2) and (3)
19.9 answer Wittig Reaction
Ph

Ph
1. 2.
O O
+ PPh3 PPh3
Ph H +
Ph
Ph

3.
O
4.
+ PPh3 Both (1) and (2)
Ph Ph

5.
Both (2) and (3)
19.10 O
1. (CH 3)2CuLi

2. H3 O+

HO CH3 OH
H3C
(a) (b)

O
O
CH 3 (d)
(c)

CH 3
19.10 answer Organocuprate 
conjugate Addition

HO CH3 OH
H3C
(a) (b)

O O

(c) CH 3 (d)

CH 3