第八章卤代烃习题解答
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NaOH/H2O
OH
Mg/Et2O
MgBr Br
Na
n-C8H18
NaOC2H5/C2H5OH
OC2H5
Na
NaI/acetone
I Br
NaOH/C2H5OH
NH3
NH2
NaCN/C2H5OH
CN
5、按要求排列 (1)写出下列化合物与 写出下列化合物与CH OH发生亲和取代反 (1)写出下列化合物与CH3ONa/CH3OH发生亲和取代反 应的速率由大到小排列
Cl
H CH3
Cl
3-氯乙苯
(4R)(4R)-4-氯-3-氯甲基-1-溴-2-戊烯 氯甲基-
CHCl2CH=CBrCH=CHCH2CH(C2H5)CH2CH3
2,47-乙基- 1,1-二氯-3-溴-2,4-壬烯 乙基- 1,1-二氯CH3 H H Br Br CH2CH3 Cl Br CH3 H H CH2CH2CH3
13、由制定原料和不超过3个碳原子 的有机试剂合成下列化合物
Cl Br
Br Cl Br Cl
Br
Cl
CH3
CH2OH CH3
CH3 CH3 CH2OH CH3 CH2Cl CH3 CH3
CH3 CH3
CH3
CH3
CH2OH Br
NO2 CH2OH Br CH2Cl Br CH3 Br
NO2 CH3
第八章 卤代烃习题解答
2、用系统命名法命名下列化合物
CH(CH3)2
(CH3)2CHCH2CHClCH3
H3CH2C Br
CH(CH3)CH2CH3
2-甲基-4-氯戊烷 甲基-
2,4-二甲基- 乙基2,4-二甲基-3-乙基-3-溴己烷
Br H3C H Cl Cl H Cl
H CH3 H Cl C2H5 C2H5 H Cl
Cl CH3 CH3
Cl2(1mol) hv
CH3
CH
3
H3CHC
CCH2Cl Br
KI
H3CHC
CCH2I Br
C2H5OH Mg CH3CH2CH2Br (C2H5)2O C2H5Br Na2CO3/EtOH
HC CCH3
CH3CH2CH3
NH2
N(C2H5)3Br
Cl
CN
+ NaCN
NO2 H
NO2 CH3
NO2
NO2
O
OH
O
MgCl
+
CH3
H3C
CH2CHCH2CH3 OH
H3C
CH2CHCH2CH3 OH H3C
CH3CH2CHO
CH2MgCl
Mg/Et2O
H3C CH2Cl
CH2O
H3C
HCl/ZnCl2
Br
CH3CH2CH3
Br
Br Br
HBr/peroxide
Br Br
+
H CH2CH2OH H CH2CH2OH
A HCl HBr peroxide
B
C2H5 H CH2CH2Br Cl CH3
C
C2H5 BrH2CH2C Cl CH3 H H
CH2CH3 H CH2CH2Br CH2CH2Br
H
E
F
D
CH3 H Br H
CH3 Br
Br
CH2Br
A
B
C
暂时无解第四题
Mg
CH2CH2Cl
CH3C
CCH2Br CH2CH2CH2C CCH3
(C2H5)2O
Br
Me2CuLi
Br
CH3
CH3
CH3
CH3C
CNa CH3
Cl
CH3C
CMgBr +
CH3COCH3
CH3COCH3
NH4Cl/H2O
HO
Cl
Br
Mg Et2O
Cl
MgBr
COONa
COONa
NaOH
Cl
HO
KOH EtOH
Br Cl
NaOH EtOH
(CH3)2CHMgBr
OH
CH3CHO
H2O
(CH3)2CHCHCH3
OH OH
NaOH/H2O
Cl
OH
CH3 H H H3C Br H CH2CH3 CH3
KOH EtOH
H3CH2C CH3
Br H H3C H CH3 CH2CH3 Br H3CH2C CH3 H H CH3
NO2 I Br
KI CH3COCH3
H
NO2
NO2
NaOCH3 CH3OH
Cl Cl OCH3 Cl
ClCH2CH2CHCH2CH3 + NaI(1mol)
Cl
ICH2CH2CHCH2CH3
Cl
DMF (CH3)2NCH2CH2CH2CH2I
N+
I-
Br
KOH, EtOH
Br Br
LiAlH4 THF
CH2Br CH2Br Br Br NO2 Br
OH发生消除反应 （2）KOH/C2H5OH发生消除反应
Br Br
CH3CH2CCH3
CH3
CH3CHCH2CH3
CH3CH2CH2ຫໍສະໝຸດ BaiduH2Br
7、用简便的化学方法区别下列各组化合物 、
Cl
CH2Cl
AgNO3/C2H5OH
(+)
立刻生成
CH2CH2Cl
(+)
加热后生成
(+)
(+)
Br2/CCl4
(-)
KMnO4 cool,dilute
(-)
(+)
(-)
Cl
(-)
AgNO3/C2H5OH
Br
(+)
加热后 室温下
(+)
I
Cl
室温下， (+) 室温下，立即
AgNO3/C2H5OH
(-)
Cl
(+)
Cl
加热、回流 加热、
9、完成下列反应
CH3 H3C CH3 ONa
CH3 Cl H CH2CH3
1,35-溴-1,3-环己二烯
H3C H Cl Br H Cl
(2S,3S)-2,3(2S,3S)-2,3-二氯戊烷
H CH3 H Br Cl H CH2CH3 CH3
C2H5
C2H5 H
Br
(2S,3S)(2S,3S)-2-氯-3-溴戊烷
CH2Br
H
CH2Cl
H3CH2C
NaOH,H2O CH3CHCHCH3
Br CH3
CH3CHCHCH3
OH CH3
KOH,EtOH
CH3CH=C(CH3)2
11推测下列化合物的结构
Br2 hv A
CHO
Br
KOH/EtOH
B
C
1 O3 2 Zn
CHO
CH2CH3
CH2CH3
CH2CH3
OH-/H2O
H CH2CH2Br
H2/Pt
MgBr
CH3CH2CH3
(CH2=CHCH2)2CuLi
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br Br
Cl
Cl
Cl
Cl
Cl
Cl
Cl2
Cl Cl Cl Cl Cl Cl Cl
+ CH3CH2CH2Br
O
Cl
CH2Br
NaCN
Cl
CH2CN
H
CH3
H
CH3
(CH3)3CBr
H2O CH3COCH3
(CH3)3COH
Br
Na2CO3 H2O
OH
CH3CH2CH
CH2Br CH2Br
Zn
CH3(CH2)4CH2Br
Mg (C2H5)2O
D2O
CH3(CH2)4CH2D
Cl
Cl
2,32,3-二溴戊烷
2-氯-3-溴己烷
Br
CH3CHCHCH2CH2CH3
CH2Cl
BrH2CC Br
CHCl
3-氯甲基-2-溴己烷 氯甲基Cl Br
1-氯-2,3-二溴丙烯 2,3CH3 Br
3-氯环己烯
NO2
2,6-二溴2,6-二溴-4-硝基甲苯
4、写出1-溴丁烷与下列试剂反应的反应式 写出1
OH
Mg/Et2O
MgBr Br
Na
n-C8H18
NaOC2H5/C2H5OH
OC2H5
Na
NaI/acetone
I Br
NaOH/C2H5OH
NH3
NH2
NaCN/C2H5OH
CN
5、按要求排列 (1)写出下列化合物与 写出下列化合物与CH OH发生亲和取代反 (1)写出下列化合物与CH3ONa/CH3OH发生亲和取代反 应的速率由大到小排列
Cl
H CH3
Cl
3-氯乙苯
(4R)(4R)-4-氯-3-氯甲基-1-溴-2-戊烯 氯甲基-
CHCl2CH=CBrCH=CHCH2CH(C2H5)CH2CH3
2,47-乙基- 1,1-二氯-3-溴-2,4-壬烯 乙基- 1,1-二氯CH3 H H Br Br CH2CH3 Cl Br CH3 H H CH2CH2CH3
13、由制定原料和不超过3个碳原子 的有机试剂合成下列化合物
Cl Br
Br Cl Br Cl
Br
Cl
CH3
CH2OH CH3
CH3 CH3 CH2OH CH3 CH2Cl CH3 CH3
CH3 CH3
CH3
CH3
CH2OH Br
NO2 CH2OH Br CH2Cl Br CH3 Br
NO2 CH3
第八章 卤代烃习题解答
2、用系统命名法命名下列化合物
CH(CH3)2
(CH3)2CHCH2CHClCH3
H3CH2C Br
CH(CH3)CH2CH3
2-甲基-4-氯戊烷 甲基-
2,4-二甲基- 乙基2,4-二甲基-3-乙基-3-溴己烷
Br H3C H Cl Cl H Cl
H CH3 H Cl C2H5 C2H5 H Cl
Cl CH3 CH3
Cl2(1mol) hv
CH3
CH
3
H3CHC
CCH2Cl Br
KI
H3CHC
CCH2I Br
C2H5OH Mg CH3CH2CH2Br (C2H5)2O C2H5Br Na2CO3/EtOH
HC CCH3
CH3CH2CH3
NH2
N(C2H5)3Br
Cl
CN
+ NaCN
NO2 H
NO2 CH3
NO2
NO2
O
OH
O
MgCl
+
CH3
H3C
CH2CHCH2CH3 OH
H3C
CH2CHCH2CH3 OH H3C
CH3CH2CHO
CH2MgCl
Mg/Et2O
H3C CH2Cl
CH2O
H3C
HCl/ZnCl2
Br
CH3CH2CH3
Br
Br Br
HBr/peroxide
Br Br
+
H CH2CH2OH H CH2CH2OH
A HCl HBr peroxide
B
C2H5 H CH2CH2Br Cl CH3
C
C2H5 BrH2CH2C Cl CH3 H H
CH2CH3 H CH2CH2Br CH2CH2Br
H
E
F
D
CH3 H Br H
CH3 Br
Br
CH2Br
A
B
C
暂时无解第四题
Mg
CH2CH2Cl
CH3C
CCH2Br CH2CH2CH2C CCH3
(C2H5)2O
Br
Me2CuLi
Br
CH3
CH3
CH3
CH3C
CNa CH3
Cl
CH3C
CMgBr +
CH3COCH3
CH3COCH3
NH4Cl/H2O
HO
Cl
Br
Mg Et2O
Cl
MgBr
COONa
COONa
NaOH
Cl
HO
KOH EtOH
Br Cl
NaOH EtOH
(CH3)2CHMgBr
OH
CH3CHO
H2O
(CH3)2CHCHCH3
OH OH
NaOH/H2O
Cl
OH
CH3 H H H3C Br H CH2CH3 CH3
KOH EtOH
H3CH2C CH3
Br H H3C H CH3 CH2CH3 Br H3CH2C CH3 H H CH3
NO2 I Br
KI CH3COCH3
H
NO2
NO2
NaOCH3 CH3OH
Cl Cl OCH3 Cl
ClCH2CH2CHCH2CH3 + NaI(1mol)
Cl
ICH2CH2CHCH2CH3
Cl
DMF (CH3)2NCH2CH2CH2CH2I
N+
I-
Br
KOH, EtOH
Br Br
LiAlH4 THF
CH2Br CH2Br Br Br NO2 Br
OH发生消除反应 （2）KOH/C2H5OH发生消除反应
Br Br
CH3CH2CCH3
CH3
CH3CHCH2CH3
CH3CH2CH2ຫໍສະໝຸດ BaiduH2Br
7、用简便的化学方法区别下列各组化合物 、
Cl
CH2Cl
AgNO3/C2H5OH
(+)
立刻生成
CH2CH2Cl
(+)
加热后生成
(+)
(+)
Br2/CCl4
(-)
KMnO4 cool,dilute
(-)
(+)
(-)
Cl
(-)
AgNO3/C2H5OH
Br
(+)
加热后 室温下
(+)
I
Cl
室温下， (+) 室温下，立即
AgNO3/C2H5OH
(-)
Cl
(+)
Cl
加热、回流 加热、
9、完成下列反应
CH3 H3C CH3 ONa
CH3 Cl H CH2CH3
1,35-溴-1,3-环己二烯
H3C H Cl Br H Cl
(2S,3S)-2,3(2S,3S)-2,3-二氯戊烷
H CH3 H Br Cl H CH2CH3 CH3
C2H5
C2H5 H
Br
(2S,3S)(2S,3S)-2-氯-3-溴戊烷
CH2Br
H
CH2Cl
H3CH2C
NaOH,H2O CH3CHCHCH3
Br CH3
CH3CHCHCH3
OH CH3
KOH,EtOH
CH3CH=C(CH3)2
11推测下列化合物的结构
Br2 hv A
CHO
Br
KOH/EtOH
B
C
1 O3 2 Zn
CHO
CH2CH3
CH2CH3
CH2CH3
OH-/H2O
H CH2CH2Br
H2/Pt
MgBr
CH3CH2CH3
(CH2=CHCH2)2CuLi
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br Br
Cl
Cl
Cl
Cl
Cl
Cl
Cl2
Cl Cl Cl Cl Cl Cl Cl
+ CH3CH2CH2Br
O
Cl
CH2Br
NaCN
Cl
CH2CN
H
CH3
H
CH3
(CH3)3CBr
H2O CH3COCH3
(CH3)3COH
Br
Na2CO3 H2O
OH
CH3CH2CH
CH2Br CH2Br
Zn
CH3(CH2)4CH2Br
Mg (C2H5)2O
D2O
CH3(CH2)4CH2D
Cl
Cl
2,32,3-二溴戊烷
2-氯-3-溴己烷
Br
CH3CHCHCH2CH2CH3
CH2Cl
BrH2CC Br
CHCl
3-氯甲基-2-溴己烷 氯甲基Cl Br
1-氯-2,3-二溴丙烯 2,3CH3 Br
3-氯环己烯
NO2
2,6-二溴2,6-二溴-4-硝基甲苯
4、写出1-溴丁烷与下列试剂反应的反应式 写出1