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按指定原料合成下列化合物（无机试剂、苯及两个碳以下（含两个碳）的有机物任选）
CH3CH CH2
CH3CH CHCHO
CH3CHCOOH
CH2COOH
OH
CH3CHCHCHO
OH
CH3
C CH2CH3
OH
O CH2CH3
CH3
Br
Br
Br
OH
COOCH2CH2CH3
COOH
NO2
COOH
NO2
Br
CHO
CH3CH=CH2
CH=CHCOOH
CH3CHCH 3
HO CHCH 3
H2NCH2CH2CH2CH2NH2
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CH2CH2CH2CH3
H2NCH2CH2CH2CH2NH2
CH2CH2CH2CH3
CH3CH2CH=CH2
CH3CH=CHCH3
CH2OH
CH2OH
CH2=CHCH=CH2
NH2
CH3
N
N
Cl
OCH2COOH
CH2=CHCH=CH2
OH
CHPh
CH2=CHCH=CH2
OH
CHPh
O
H3CHC
O
O
CHCH 3
O
PhCH2CH2COOH
N=N
CH2=CHCH=CH2
H2N
H2N
NH2
COOC2H5
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CH3CH2C
OH
CC Ph
CH3
CH3
CHCH
CH3
CH3(CH2)6CH3
1. CH3CH CH2
CH3CHCOOH
CH2COOH
Br2
a) NaCN
b)H3+O
CH3CH CH2Br
Br
OH
CH3CHCHCHO
OH
2. CH3CH CHCHO
HCl/HOCH2CH2OH
a)KMnO4/OH-
O
b)
CH3CH CHCH
H3+O
O
CH3
C CH2CH3
OH
3.
CH3COCl/AlCl3
a) CH3CH2MgBr/无水Et2O
COCH3
b) H3+O
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4.
O CH2CH3
a) 混酸
b)Fe/HCl
c)NaNO2/HCl
d)H2O/OH-
CH3CH2Br/NaOH
OH
5.
CH3
Br
Br
Br
a) KMnO4
b)NH3
c)Fe/HCl
a)Br2/H2O
b)NaNO2/HCl
NH2
6.
c)HPO2
OH
a)KMnO4
b)HCN
c) H3+O/
COOCH2CH2CH3
H2SO4/CH3CH2CH2OH
LiAlH4
CH3CH2COOH
COOH
a)NaCN
b) H3+O
CH3CH2Br
COOH
7.
NO2
a)CH3I/AlCl3
b)KMnO4
混酸
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COOH
8.
NO2
a)CH3I/AlCl3
b)Fe/Br2
c) KMnO4
Br
COOH
混酸
Br
9.
CHO
CH=CHCOOH
CH3CHO/稀NaOH
Tollen试剂
CH=CHCHO
10.
CH3CH=CH2
CH3CHCH 3
HO CHCH 3
a)HBr
b) Mg/无水Et2O
a)CH3CHO
b) H +O
3
CH3CHCH 3
MgBr
11.
H2NCH 2CH2CH2CH2NH2
a) KMnO4
b)NH3/
Br2/NaOH
NH2CO(CH 2)4CONH2
CH2CH2CH2CH3
12.
CH3CH2CH2COCl/AlCl3
CCH 2CH2CH3
O
CH3CHO
稀NaOH
CH3CH2CH2COCl
Zn-Hg/HCl
CH3CH=CHCHO
a)KMnO4
b)SOCl2
H2/Ni
CH3CH2CH2CH2OH
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13.
CH3CH2CH=CH2
CH3CH=CHCH3
HBr
KOH/CH3CH2OH/
CH3CH2CHCH 3
Br
14.
CH2OH
CH2OH
CH2=CHCH=CH2
Br2
a) CH2=CHCH=CH2
BrCH2CH=CHCH2Br
b)LiAlH4
NaOH/H2O
HOCH2CH=CHCH2OH
Cu/
OHCCH=CHCHO
N=N
CH3
15.
NH2
N
N
a)混酸
a)KMnO4
NH2
b)NH3/
c)Br2/NaOH
NH2
NaNO2/HCl
N2+Cl -
N
N
Cl
16.
OCH2COOH
a) Fe/Cl2
a) NaOH
b) ClCH2COOH
b) 混酸
c) Fe/HCl
a) NaNO2/HCl
NH2
Cl
b)Fe/HCl
b) H2O/OH-
OH
Cl
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17.
OH
CHPh
CH2=CHCH=CH2
CH2=CHCHO
a) PhMgBr/无水Et2O
b) H3+O
CHO
HCHO
NaOH
CH3CHO
CH2=CHCHO
O
CH3CCHCH 2Ph
CH3
18.
CH3I/AlCl3
Cl2/hv
CH3
CH3COOH
CH2Cl
CH3CH2OH
CH3COOC2H5
H+
NaOC2H5
O
CH3CCH 2COOC2H5
a) NaOC2H5
O
CH3CCHCH 2Ph
CH3
a) NaOC2H5
b) PhCH2Cl
c) H3+O
b) CH3I
O
CH3CCHCOOC 2H5
CH3
d)
19.
O
H3CHC
O
O
CHCH 3
O
HCHO
CH3CHO
稀NaOH
浓NaOH
(HOCH 2)3CCHO
HCHO
(HOCH 2)4C
CH3CHO/HCl
O
H3CHC
O
O
CHCH 3
O
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20.
PhCH2CH2COOH
a) CH3I/AlCl3
b) Fe/Cl2
CH2Cl
a) NaCN
+
b) H3 O
ClCH2COOH
COOC2H5
+
c) CH3CH2OH/H
H2C
COOC2H5
21.
a) NaOC2H5
b) PhCH2Cl
c) H3+O
d)
NH2
N=N
a) 混酸
b)Fe/HCl
NH2
a) NaNO2/HCl
TM
b) PhNH2
22.
COOC2H5
H2N
H2N
CH2=CHCH=CH2
CH2=CHCOOC2H5
NH3
COOC2H5
CH3CH2C
23.
COOC2H5
Br
Br
Br2
OH
CC Ph
CH3
CH3COCl/AlCl3
a) Na/NH3
COCH3
HC CH
b) CH3CH2C CH
a) Na/NH3
b) CH3CH2Br
CH3CH2C
CH
TM
PhCH2CH2COOH
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CH3
CHCH
CH3
24.
CH3CH2Cl/AlCl3
CH2CH3
25.
Na
Cl2/hv
CHCH 3
Cl
CH3(CH 2)6CH3
CH3CHO
稀NaOH
CH3CH=CHCHO
H2/Ni
CH3CH2CH2CH2OH
PBr3
Na
CH3(CH 2)6CH3
CH3CH2CH2CH2Br