Transcript Document

1)
O
OH
NaBH4
H
H
OH
OH
+
1
2)
O
LiAlH4
OH
O
3)
O
HO
PhMgBr
2
4)
O
Tollens reagent
No reaction
Ag2O and NH4OH are the Tollens reagent
5)
O
HO
Na
3
6) Draw sodium acetate.
O
O
Na
7) Draw cycloheptanecarboxylic acid.
O
OH
4
8)
Draw 4-hexenal.
O
O
9) Draw 2,4-pentanedione.
O
O
5
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
+
6
12) Draw the product(after workup) of 3-methyl2-cyclohexenone with H2./Pd-C.
O
O
H2/Pd-C
H
H
O
O
+
13) Draw the keto tautomer of this enol.
OH
OH
OH
O
H
H
7
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
The Z isomer is preferred due to the
stabilization provided by hydrogen
bonding.
O
OH
O
+
O
HO
8
15)
OH
OH
LiAlH4
O
16)
HO
O
excess PhMgBr
Cl
dilute acid
9
17)
O
OH
LiAlH4
OCH2CH3
18)
O
O
OH
excess PhMgBr
HO
10
O
O
O
O
OH
H2O
O
HO
O
11
19)
HO
O
excess PhMgBr
H3CH2CO
OCH2CH3
O
H3CH2CO
O
OCH2CH3
Ph
H3CH2CO
O
OCH2CH3
Ph
H3CH2CO
Ph
Ph
12
O
O
Ph
O
Ph
H3CH2CO
Ph
Ph
Ph
Ph
Ph
Ph
H2O
OH
Ph
Ph
Ph
13
20)
Na2Cr2O7
O
H2SO4
OH
OH
14
19..29a) Draw 3,3’-dimethylpentanoic acid.
O
OH
e) Draw m-hydroxybenzoic acid
O
HO
OH
15
19.32a)
O
OH
CrO3
OH
H2SO4, H2O
b)
KMnO4
O
O
HO
OH
c)
O3
H2O
O
+
O
C
OH
16
O
d)
R
H2
C
Na2Cr2O7
O
H2SO4, H2O
C
OH
R
OH
19.33a)
BH3
H2O2, -OH
b)
NaNH2
CH3I
O
CrO3
OH
H2SO4, H2O
OH
NaNH2
H3CH2C
CH3
CH3CH2I
O3
H2O
O
O
+
OH
17
OH
c)
O
(CH3)2CHCl
KMnO4
OH
AlCl3
.
18
19.37) In each group choose which compound is most acidic. Also
choose which has the strongest conjugate base.
a)
O
O
O
OH
Strongest
conjugate base
b)
Cl
Br
Most acidic
OH
OH
OH
Cl
O2N
Strongest
conjugate base
OH
OH
Most acidic
19
20.37)
O
NaBH4
MeOH
OH
LiAlH4
H2O
H2/Pd-C
PCC
No reaction
Na2Cr2O7
H2SO4, H2O
O
Ag2O
OH
NH4OH
20
OH
O CH3MgBr
H2O
CH3Li
H2O
(CH3)2CuLi
H2O
CNa
No reaction
OH
H2O
CLi
H2O
TBDMSCl
O
imidazole
OTBDMS
21
20.38)
O
NaBH4
MeOH
OH
LiAlH4
H2O
H2/Pd-C
PCC
Na2Cr2O7
No reaction
H2SO4, H2O
Ag2O
NH4OH
22
O
CH3MgBr
OH
H2O
CH3Li
H2O
CNa
H 2O
HO
CNa
H 2O
TBDMSCl
No reaction
imidazole
23
20.40)
MgBr
H3CH2C
OH
+
H3CH2C
O
O
CO2
H3O+
OH
O
OH
24
O
20.41)
O
Cl
R2CuLi
R
O
OEt
R2CuLi
No reaction
O
O
R2CuLi
R
OH
O
R2CuLi
R
25
20.47)
OH
O
NaBH4
O
MeOH
O
OCH3
OH
LiAlH4
OCH3
OH
H2O
O
O
(H3C)2N
OH
LiAlH4
(H3C)2N
H2O
OH
O
O
OH
LiAlH
(OC(CH3)3)3
H2O
Cl
HO
OH
O
26
21.46)
OH
NaCN
HCl
O
CN
Ph3P
CHCH3
(H3C)2HC
NH2
H3 O+
NCH(CH3)2
27
H
N
H3CH2C
CH2CH3
O
N(CH2CH3)2
H3 O+
OCH2CH3
excess EtOH
TsOH
OCH2CH3
HO
O
OH
TsOH
O
28
21.54)
Br
Br
Br2
CH3COCl
O
FeBr3
AlCl3
OH
HO
O
O
Mg
O
TsOH
MgBr
Br
O
29
O
O
O
MgBr
O
O
H2O
O
H 2O
OH
H 3O +
O
PCC
O
O
O
30
1)
O
O
H2O
NH2
NH
HCl, heat
OH
31
H
O
Cl
OH
HO
H2O
H
O
H
NH
NH
NH
HO
Cl
HO
OH
OH
H
NH2
Cl
NH
Cl
O
HO
NH2
NH2
OH
OH
32
2)
O
O
H2O
O
O
HO
OH
O
33
3)
O
O
excess CH3OH
O
O
HCl
O
O
O
34
4)
aq. H2O
20 C
O
CN
H2N
35
5)
O
NH2
OCH2CH3
H
N
O
36
6)
O
excess H2O
O
O
HO
HCl
OH
37
7)
O
O
excess NH3
NH2
O
OH
O
O
38
8)
O
O
CH3CH2OH
Cl
O
39
9)
OH
O
O
O
O
O
40
10)
NH2
O
O
N
H
O
OH
O
O
41
11)
O
O
CH3NH2
OCH3
NHCH3
42
12)
O
O
OH
OCH2CH2CH3
O
O
SOCl2
OH
O
CH3CH2CH2OH
Cl
Cl
O
OCH2CH2CH3
43
13)
O
O
NH2
Cl
O
O
H2O
NH2 H+, heat
O
OH
O
SOCl2
OH
Cl
44
14)
OH
OH
O
SOCl2
Cl
OH
NaCN
N
Cl
N
H2O
OH
H+, heat
O
45
O
15)
N
H
O
KMnO4
OH
heat
O
O
SOCl2
OH
Cl
46
O
O
excess NH3
Cl
NH3
47
22.53)
a)
O
O
OH
Cl
SOCl2
OH
OH
b)
O
O
NH
Cl
N
excess
48
c)
CN
O
CH3CH2CH2MgBr
H2O
CH2CH2CH3
d)
O
O
OH
OH
O
49
e)
H
N
O
NH2
H2O
NaOH
f)
O
O
O
OH
H3O+
OH
O
O
50
g)
NaCN
O
Br H O, NaOH
2
O
h)
O
SOCl2
OH
CH3CH2CH2CH2NH2
HN
LiAlH4
H2O
51
i)
CN
O
H 3O +
C
OH
j)
O
heat
O
O
O
OH HO
O
52
k)
O
O
H
N
NH2
O
O
l)
O
O
O
H2O
O
NaOH
53
22.54)
H3O+
NaCN
Br
O
CN
HO
SOCl2
(CH3)2CuLi
O
H 2O
O
Cl
54
LiAlH4
CN
H2O
NH2
(CH3CO)2O
O
NH
55
O
CH3OH
O
O
H+
HO
DIBAL-H
H2O
CH3Li
OH
H2O
O
PCC
O
56
O
LiAlH4
H2O
O
OH
TsOH
pyridine
NaCN
CN
CH3MgBr
OTs
H2O
O
57