1
O
NaBH
4
1)
OH
OH
OH
H
H
+
1
O
NaBH
4
1)
OH
OH
OH
H
H
+
2
O
O
LiAlH
4
OH
2)
O
PhMgBr
HO
3)
3
O
Tollens reagent
No reaction
Ag
2
O and NH
4
OH are the Tollens
reagent
4)
O
Na
HO
5)
4
6) Draw sodium acetate.
O
O
Na
7) Draw cycloheptanecarboxylic
acid.
O
OH
5
8) Draw 4-hexenal.
O
O
9) Draw 2,4-
pentanedione.
O
O
6
10) Draw benzene-1,3-
dicarboxaldehyde.
O
O
11) Draw the product(after workup) of 3-methyl-2-
cyclohexenone with methyl Grignard.
O
MgBr
HO
HO
HO
+
7
12) Draw the product(after workup) of
3-methyl-2-cyclohexenone with H
2
./Pd-
C.
O
H
2
/Pd-C
O
O
O
+
H
H
13) Draw the keto tautomer of this
enol.
OH
OH
H
OH
H
O
8
14) Pentane-2,4-dione exists as a tautomeric mixture
of 8% keto and 92% enol. Draw the enol form.
O
O
O
O
O
O
OH
O
HO
O
+
The Z isomer is preferred due
to the stabilization provided
by hydrogen bonding.
9
15)
O
OH
LiAlH
4
OH
O
Cl
excess PhMgBr
dilute acid
16)
HO
10
17
)
O
OCH
2
CH
3
LiAlH
4
OH
18)
O
O
excess PhMgBr
HO
OH
11
O
O
O
O
O
O
H
2
O
HO
OH
12
19)
H
3
CH
2
CO
O
OCH
2
CH
3
excess PhMgBr
HO
H
3
CH
2
CO
O
OCH
2
CH
3
Ph
H
3
CH
2
CO
O
OCH
2
CH
3
Ph
H
3
CH
2
CO
O
Ph
Ph
13
H
3
CH
2
CO
O
Ph
Ph
Ph
O
Ph
Ph
Ph
O
Ph
Ph
H
2
O
Ph
OH
Ph
Ph
14
20)
OH
Na
2
Cr
2
O
7
H
2
SO
4
OH
O
15
19..29a) Draw 3,3’-dimethylpentanoic
acid.
e) Draw m-hydroxybenzoic acid
O
OH
HO
O
OH
16
19.32
a)
OH
CrO
3
H
2
SO
4
, H
2
O
OH
O
b)
KMnO
4
O
HO
O
OH
c)
O
3
H
2
O
OH
O
+
O
C
O
17
d)
R
H
2
C
OH
Na
2
Cr
2
O
7
H
2
SO
4
, H
2
O
R
C
OH
O
BH
3
H
2
O
2
, -OH
19.33a)
OH
CrO
3
H
2
SO
4
, H
2
O
OH
O
b)
NaNH
2
CH
3
I
NaNH
2
CH
3
CH
2
I
H
3
CH
2
C
CH
3
O
3
H
2
O
O
OH
O
OH
+
18
c)
(CH
3
)
2
CHCl
AlCl
3
KMnO
4
O
OH
.
19
19.37) In each group choose which compound is
most acidic. Also choose which has the strongest
conjugate base.
a)
O
OH
O
OH
O
OH
Br
Cl
Most acidic
Strongest
conjugate
base
b
)
OH
O
2
N
OH
Cl
OH
Most acidic
Strongest
conjugate
base
20
O
H
2
/Pd-C
NaBH
4
MeOH
LiAlH
4
H
2
O
20.3
7)
OH
PCC
OH
O
No
reaction
Na
2
Cr
2
O
7
H
2
SO
4
, H
2
O
Ag
2
O
NH
4
OH
21
O
CH
3
MgBr
H
2
O
CH
3
Li
H
2
O
(CH
3
)
2
CuLi
H
2
O
CNa
H
2
O
CLi
H
2
O
TBDMSCl
imidazole
OH
No reaction
OH
OTBDMS
O
22
20.38)
H
2
/Pd-C
NaBH
4
MeOH
LiAlH
4
H
2
O
O
OH
PCC
Na
2
Cr
2
O
7
H
2
SO
4
, H
2
O
Ag
2
O
NH
4
OH
No reaction
23
CH
3
MgBr
H
2
O
CH
3
Li
H
2
O
O
OH
CNa
H
2
O
CNa
H
2
O
HO
TBDMSCl
imidazole
No reaction
24
20.40)
MgBr H
3
CH
2
C
OH
CO
2
H
3
O
+
O
+
H
3
CH
2
C
O
OH
O
OH
25
20.41)
O
Cl
R
2
CuLi
R
2
CuLi
O
OEt
R
2
CuLi
O
R
2
CuLi
O
O
R
No reaction
O
R
OH
R
26
20.4
7)
NaBH
4
MeOH
LiAlH
4
H
2
O
LiAlH
4
H
2
O
O
O
OCH
3
OH
O
OCH
3
OH
OH
(H
3
C)
2
N
OH
(H
3
C)
2
N
O
O
OH
Cl
O
O
OH
LiAlH
(OC(CH
3
)
3
)
3
H
2
O
HO
O
OH
27
21.46)
O
NaCN
HCl
Ph
3
P
CHCH
3
(H
3
C)
2
HC
NH
2
H
3
O
+
OH
CN
NCH(CH
3
)
2
28
O
CH
2
CH
3
H
N
H
3
O
+
H
3
CH
2
C
excess EtOH
TsOH
HO
OH
TsOH
N(CH
2
CH
3
)
2
OCH
2
CH
3
OCH
2
CH
3
O
O
29
21.54)
Br
2
FeBr
3
Br
CH
3
COCl
AlCl
3
Br
O
HO
OH
TsOH
Br
O
O
Mg
MgBr
O
O
30
MgBr
O
O
O
H
2
O
O
O
OH
PCC
O
O
O
H
2
O
H
3
O
+
O
O
31
NH
O
H
2
O
HCl, heat
1)
NH
2
O
OH
32
NH
O
H
Cl
NH
OH
H
2
O
NH
HO
H
O
H
Cl
NH
HO
OH
H
Cl
NH
2
HO
OH
NH
2
HO
OH
Cl
NH
2
O
OH
33
2)
O
O
O
H
2
O
O
HO
O
OH
34
3)
O
O
O
excess CH
3
OH
HCl
O
O
O
O
35
4)
CN
aq. H
2
O
20 C
O
H
2
N
36
5)
NH
2
O
OCH
2
CH
3
H
N
O
37
O
O
excess H
2
O
HCl
6)
O
HO
OH
38
7
)
O
O
O
excess NH
3
O
NH
2
O
OH
39
8)
O
Cl
CH
3
CH
2
OH
O
O
40
9)
OH
O
O
O
O
O
41
10
)
NH
2
O
O
O
O
N
H
O
OH
42
11)
O
OCH
3
CH
3
NH
2
O
NHCH
3
43
12
)
O
OH
O
OCH
2
CH
2
CH
3
O
OH
O
Cl
SOCl
2
O
Cl
O
OCH
2
CH
2
CH
3
CH
3
CH
2
CH
2
OH
44
13
)
O
NH
2
O
Cl
O
NH
2
O
OH
H
2
O
H
+
, heat
O
OH
O
Cl
SOCl
2
45
14)
OH
O
OH
OH
Cl
SOCl
2
Cl
NaCN
N
N
H
2
O
H
+
, heat
O
OH
46
15)
O
N
H
O
OH
KMnO
4
heat
O
OH
O
Cl
SOCl
2
47
O
Cl
excess NH
3
O
NH
3
48
22.53
)
a)
O
OH
OH
SOCl
2
O
Cl
OH
b)
O
Cl
NH
excess
O
N
49
c
)
d
)
CN
CH
3
CH
2
CH
2
MgBr
H
2
O
O
CH
2
CH
2
CH
3
O
OH
OH
O
O
50
e)
H
N
O
H
2
O
NaOH
NH
2
f)
O
O
O
H
3
O
+
O
O
OH
OH
51
g)
h
)
Br
NaCN
H
2
O, NaOH
O
O
O
OH
SOCl
2
CH
3
CH
2
CH
2
CH
2
NH
2
LiAlH
4
H
2
O
HN
52
i)
j)
CN
H
3
O
+
C
O
OH
O
OH
O
HO
heat
O
O
O
53
k
)
l
)
O
O
O
NH
2
H
N
O
O
O
H
2
O
NaOH
O
O
54
22.54)
Br
NaCN
CN
H
3
O
+
O
HO
SOCl2
O
Cl
(CH
3
)
2
CuLi
H
2
O
O
55
CN
LiAlH
4
H
2
O
NH
2
(CH
3
CO)
2
O
NH
O
56
O
HO
CH
3
OH
H
+
O
O
DIBAL-H
H
2
O
O
CH
3
Li
H
2
O
OH
PCC
O
57
O
O
LiAlH
4
H
2
O
OH
TsOH
pyridine
OTs
NaCN
CN
CH
3
MgBr
H
2
O
O