Reactions of Aldehydes and Ketones

OH
OH
A
A
RO C O H(R) RO C O H(R)
A
A
H
R

CH2H(R)

OH
OH
OR
SR
H R
A
A
A
A
N
NR2
G
B
RO C O H(R) RO C O H(R) RO C O H(R) RO C O H(R)
RCH P C
A
A
A
A
C
D
E H
R
OH
OR
OR
SR
R
H(R)

Substrate:
RC6H5

NaBH4
or
LiAlH4

RLi
or
RMgX

Substrate:
O
B
RCH2CR

Zn(Hg), HCl, 

H2O,
H or HO

ROH,
H or HO

ROH, H

RCOOH
B
O

O
B
EC H O
R
O H(R)

RCH2H(R)

OH
(R)H H HR(H)
A
C
B
RO C O H(R)
A
EC H
CN
R
H(R)

O
B
C
E H

RSH, H

RNH2,
H or HO

H2NNH2, H2O
HO, 

NaCN, H

HO, H2O, 

H2, PdOC

H or

Substrate:
O
B
RCH2CR

Substrate:
O
B
C
H
E
G
CP C
D
D

R2 NH,
H or HO

RCHP(C6H5)3

O
B
C
E H
HR
R

Oxidant
(i.e., CrO3, KMnO4, Ag, Cu2,
H2O2, HNO3, O2-Rh3, Br2)

CH3
A
(CH3CH)2NLi
(LDA)

H or HO,
H2O

X2, H

X2, HO

1. NaH
or
LDA
2. RX

Substrate:
O
B
C
E H
R
H

Substrate:
O
A
l
OCO C
A
i
H

Substrate:
O
A
l
OCO C
A
i
H

Substrate:
O
A
l
OCO C
A
i
H

Substrate:
H
O
A
l
OCO C
A
i
H

Substrate:
O
A
l
OCO C
A
i
H

O
B
RCOH

O
G
G
CP C
D
D

OH
G
G
CP C
D
D

O
A
J
OCOC
G
A
X

X
O
A
J
OCOC
G
A
X

O
A
J
OCOC
G
A
R

NuH,
HO

Substrate:
O
B
C
H E
G
CP C
D
D

1. R2 CuLi
2. EX
(EH, R)

Substrate:
O
B
C
H E
G
CP C
D
D

O
R R
O
A A
A A
O
J
J
A A
A A
J
OC OCOC
OC OCOC
RCH2CPCCR O C O C O C
G
G
A A
A A
G
A A
B
R E
Nu H
O
H H
(EH, R)