有机化学下课件-习题课

一、完成下列反应1.

(CH3CH2)3CCH2OH

HBr

H2SO4,△2.

CH3CH=CHC=CHCH2OHCH3

MnO2/戊烷

3.

CH

CCH2CH2CH2CHO+

MgBr3CH34.

CH

CH

C

C6H5OH

OHHIO45.OHH+一、完成下列反应1.

(CH3CH2)3CCH2OH

HBr

H2SO4,△(CH3CH2)2CCH2CH2CH3Br2.

CH3CH=CHC=CHCH2OHCH3

MnO2/戊烷

3.

CH

CCH2CH2CH2CHO+

MgBr3CH34.

CH

CH

C

C6H5OH

OHHIO45.OHH+一、完成下列反应1.

(CH3CH2)3CCH2OH

HBr

H2SO4,△(CH3CH2)2CCH2CH2CH3Br2.

CH3CH=CHC=CHCH2OHCH3

MnO2/戊烷

CH3CH=CHC=CHCHOCH3氧化生成醛，且不影响双键。3.

CH

CCH2CH2CH2CHO+

MgBr3CH34.

CH

CH

C

C6H5OH

OHHIO45.OHH+一、完成下列反应1.

(CH3CH2)3CCH2OH

HBr

H2SO4,△(CH3CH2)2CCH2CH2CH3Br2.

CH3CH=CHC=CHCH2OHCH3

MnO2/戊烷

CH3CH=CHC=CHCHOCH3氧化生成醛，且不影响双键。3.

CH

CCH2CH2CH2CHO+

MgBrBrMgCCCH2CH2CH2CHO

+3CH34.

CH

CH

C

C6H5OH

OHHIO45.OHH+一、完成下列反应1.

(CH3CH2)3CCH2OH

HBr

H2SO4,△(CH3CH2)2CCH2CH2CH3Br2.

CH3CH=CHC=CHCH2OHCH3

MnO2/戊烷

CH3CH=CHC=CHCHOCH3氧化生成醛，且不影响双键。3.

CH

CCH2CH2CH2CHO+

MgBrBrMgCCCH2CH2CH2CHO

+3CH34.

CH

CH

C

C6H5OH

OHHIO43CH

CHO

+

CH3COC6H55.OHH+一、完成下列反应1.

(CH3CH2)3CCH2OH

HBr

H2SO4,△(CH3CH2)2CCH2CH2CH3Br2.

CH3CH=CHC=CHCH2OHCH3

MnO2/戊烷

CH3CH=CHC=CHCHOCH3氧化生成醛，且不影响双键。3.

CH

CCH2CH2CH2CHO+

MgBrBrMgCCCH2CH2CH2CHO

+3CH34.

CH

CH

C

C6H5OH

OHHIO43CH

CHO

+

CH3COC6H55.OHH+OH6.OH

CHCH33CH3CH2

CH3O7.OHCN6

5C

H

CH

CH28.OCH2OHOH

,

H2O=O9.

CH3CH2CCH3

+O2N

NO2NHNH2

HOAcH

CHCH33CH3CH2OHOCH36.OH3CHCH3CH3CH2

CH3O7.OHCN6

5C

H

CH

CH28.OCH2OHOH

,

H2O=O9.

CH3CH2CCH3

+O2N

NO2NHNH2

HOAcH

CHCH33CH3CH2OHOCH36.OH3CHCH3CH3CH2

CH3O7.OHCNC6H5CH

CH2C6H5CHCH2OHCN8.OCH2OHOH

,

H2O=O9.

CH3CH2CCH3

+O2N

NO2NHNH2

HOAcH

CHCH33CH3CH2OHOCH36.OH3CHCH3CH3CH2

CH3O7.OHCNC6H5CH

CH2C6H5CHCH2OHCN8.OCH2OHOH

,

H2OOHH=O9.

CH3CH2CCH3

+O2N

NO2H2C

ONHNH2

HOAcH

CHCH33CH3CH2OHOCH36.OH3CHCH3CH3CH2

CH3O7.OHCNC6H5CH

CH2C6H5CHCH2OHCN8.OCH2OHOH

,

H2OOHH=O9.

CH3CH2CCH3

+O2N

NO2H2C

ONHNH2

HOAcC=NNH

NO2NO2CH3CH2CH311.HCH3C6H5C6H5C=O①

p-ClC6H4MgBr②

H3O+11.HCH3C6H5C6H5C=O①

p-ClC6H4MgBr②

H3O+=OH5C6

C6H5HCH3

p-ClC6H4MgBr从位阻小的左边进攻HC6H5OHCH3C6H5p-ClC6H4H3O+C6H56

4C6H5C

H

Cl-pHCH3HO=O13. CH3CH

=CHCCH2CH②

H2O+3①

CH3MgBr/CuCl=14.

CH3CCH2CH2CCH3=O

O

NaOH

-

H2O

△15. 2

PhCHO+CH3COCH3H2O

-C2H5OHNaOH16.

Br

CHO+OCH3

NaOH17.OCHO3O+

CH3CCH2CHH+O18.

CH3CCH2CH2CHO

OH=O13. CH3CH

=CHCCH2CH②

H2O+3①

CH3MgBr/CuCl=OCH3CHCH2CCH2CH3CH3=14.

CH3CCH2CH2CCH3=O

O

NaOH

-

H2O

△15. 2

PhCHO+CH3COCH3H2O

-C2H5OHNaOH16.

Br

CHO+OCH3

NaOH17.OCHO3O+

CH3CCH2CHH+O18.

CH3CCH2CH2CHO

OH=O13. CH3CH

=CHCCH2CH②

H2O+3①

CH3MgBr/CuCl==14.

CH3CCH2CH2CCH3=O

O

NaOH

-

H2O

△=OCH3CHCH2CCH2CH3CH3OCH315. 2

PhCHO+CH3COCH3H2O

-C2H5OHNaOH16.

Br

CHO+OCH3

NaOH17.OCHO3O+

CH3CCH2CHH+O18.

CH3CCH2CH2CHO

OH=O13. CH3CH

=CHCCH2CH②

H2O+3①

CH3MgBr/CuCl==14.

CH3CCH2CH2CCH3=O

O

NaOH

-

H2O

△=OCH3CHCH2CCH2CH3CH3OCH315. 2

PhCHO+CH3COCH3H2O

-C2H5OHNaOHPhCH=CHOC

CH=CHPh16.

Br

CHO+OCH3

NaOH17.OCHO+

CH3CCH2CH3考虑α－H

的酸性OH+考虑烯醇化的难易O18.

CH3CCH2CH2CHO

OH=O13. CH3CH

=CHCCH2CH②

H2O+3①

CH3MgBr/CuCl==14.

CH3CCH2CH2CCH3=O

O

NaOH

-

H2O

△=OCH3CHCH2CCH2CH3CH3OCH315. 2

PhCHO+CH3COCH3H2O

-C2H5OHNaOHOC

CH=CHPh16.

Br

CHO+OCH3

NaOHBr

CH=PhCH=CHO

CH317.OCHO+

CH3CCH2CH3考虑α－H

的酸性OH+考虑烯醇化的难易O18.

CH3CCH2CH2CHO

OH=O13. CH3CH

=CHCCH2CH②

H2O+3①

CH3MgBr/CuCl==14.

CH3CCH2CH2CCH3=O

O

NaOH

-

H2O

△=OCH3CHCH2CCH2CH3CH3OCH315. 2

PhCHO+CH3COCH3H2O

-C2H5OHNaOHOC

CH=CHPh16.

Br

CHO+OCH3

NaOHBr

CH=PhCH=CHO

CH317.OCHO+

CH3CCH2CH3考虑α－H

的酸性OH+OCH=CCCHCH33O考虑烯醇化的难易O18.

CH3CCH2CH2CHO

OH=O13. CH3CH

=CHCCH2CH②

H2O+3①

CH3MgBr/CuCl==14.

CH3CCH2CH2CCH3=O

O

NaOH

-

H2O

△=OCH3CHCH2CCH2CH3CH3OCH315. 2

PhCHO+CH3COCH3H2O

-C2H5OHNaOHOC

CH=CHPh16.

Br

CHO+OCH3

NaOHBr

CH=PhCH=CHO

CH317.OCHO+

CH3CCH2CH3考虑α－H

的酸性OH+OCH=CCCHCH33O考虑烯醇化的难易O18.

CH3CCH2CH2CHO

OHOHOH分子内羟醛缩合（2）反应机理O3CH

CCH+OHCH3C-CH2-HOHCH3C=CH2+OHCH3CCH3OHCH3-C-CH2-C(CH3)2+OH-H+OHCH3-C-CH2-C(CH3)2O-H2O酸催化下的反应机理3

H+烯醇化亲核加成酸碱反应OCH3-C-CH=C(CH3)2-H+碱催化下的反应机理CH3CH=O-CH2CH=O-B：CH3CH=OO-CH3CHCH2CHO-H2OCH3CH=CHCHO常用的碱性催化剂有：KOH，C2H5ONa，(t-BuO)3Al.催化剂用量应在0.5mol以上。OH

OCH3CHCH2CHH2O烯醇化亲核加成酸碱反应19.CH32=O

+

Br

(1

mol

)

H

O2HOAc20.

CH3CH2CH2CHCH3I2

,

NaOH过量21.OH=OHO+

CH3CCH3

HCl(气）OHCl22.CH2CH2Cl

NaOH/H2O=O3CHBr19.2CH3=O+

Br

(1

mol

)

H

O2HOAc20.

CH3CH2CH2CHCH3I2

,

NaOH过量21.OH=OHO+

CH3CCH3

HCl(气）OHCl22.CH2CH2Cl

NaOH/H2O=O3CHBr19.2CH3=O+

Br

(1

mol

)

H

O2HOAc思考：若在碱性条件下，其产物是什么？20.

CH3CH2CH2CHCH3I2

,

NaOH过量21.OH=OHO+

CH3CCH3

HCl(气）OHCl22.CH2CH2Cl

NaOH/H2O=O3CHBr19.2CH3=O+

Br

(1

mol

)

H

O2HOAc思考：若在碱性条件下，其产物是什么？20.

CH3CH2CH2CHCH3

I2

,

NaOH过量CH3CH2CH2COONa

+

CHI321.OH=OHO+

CH3CCH3

HCl(气）OHCl22.CH2CH2Cl

NaOH/H2O=O3CHBr19.2CH3=O+

Br

(1

mol

)

H

O2HOAc思考：若在碱性条件下，其产物是什么？20.

CH3CH2CH2CHCH3OH

I2

,

NaOH过量CH3CH2CH2COONa

+

CHI321.OHOH+

CH3CCH3=O

HCl(气）OOCHCH3322.ClCH2CH2Cl

NaOH/H2O=O3CHBr19.2CH3=O+

Br

(1

mol

)

H

O2HOAc思考：若在碱性条件下，其产物是什么？20.

CH3CH2CH2CHCH3OH

I2

,

NaOH过量CH3CH2CH2COONa

+

CHI321.OHOH+

CH3CCH3=O

HCl(气）OOCHCH3322.ClCH2CH2Cl

NaOH/H2OClCH2CH2OH25.OH3+CH

CClOAAlCl3△B①

C6H5CHO②

(CH3CO)2OCBr2D25.OH3+CH

CClOAAlCl3△B①

C6H5CHO②

(CH3CO)2OCBr2DOCCH3A.B.C.D.OOH

OCCH3OCCH

=CHC6H5OCCH

3OOCCHBrCHBrC6H5OCCH

3O32酚酯(亦称羧酸苯酯)与AlCl3、ZnCl2等Lewis酸共热，酰基则从酚的氧原子上转移到酚羟基的邻位或对位，生成邻羟基酮或对羟基酮，该反应称为Fries重排。CH3OCOCH3

AlCl3

C6H5NO2

,165℃

AlCl3

C6H5NO2

,25℃CH3OHCOCH3CH3OHCOCH3较高温度下,有利于邻位异构体的生成较低温度下,有利于对位异构体的生成二、按要求回答下列问题1.按酸性由强到弱排列成序：A.

H

B.

OHC.CH3OHD.

F3CCH2OHE.ClCH2CH2OHF.CH3CH2CH2CH2OHG.CH3CH2CCHH.CH3CH2CH2CH3(1)(2)OHOHOHOCH3A.OHB.OHOCH3C.ClD.NO2NO2E.2.按碱性由强到弱排列成序：二、按要求回答下列问题1.按酸性由强到弱排列成序：A.

H

B.

OHC.CH3OHD.

F3CCH2OHE.ClCH2CH2OHF.CH3CH2CH2CH2OHG.

CH3CH2CCHH.CH3CH2CH2CH3(1)DE>OHG

＞

A>

HOH(2)>OHFBC>

＞>OHOCH3A.B.OHOCH3C.ClD.NO2NO2E.2.按碱性由强到弱排列成序：二、按要求回答下列问题1.按酸性由强到弱排列成序：A.

H

B.

OHC.CH3OHD.

F3CCH2OHE.ClCH2CH2OHF.CH3CH2CH2CH2OHG.

CH3CH2CCHH.CH3CH2CH2CH3(1)DE>OHG

＞

A>

HOH(2)>OHFBC>

＞>OHOCH3A.B.OHOCH3C.Cl>

B

＞

AD.NO2NO2E.D

＞

E>C2.按碱性由强到弱排列成序：A.(CH3CH2)2CHOD.

O

E.B.

(CH3CH2)3CO

C.

O2N

F.

CH3CH2CH2OOCl

O3.按沸点由高到低排列成序：A.CH2

CH

CH2OH

OH

OHB.CH2

CH

CH2OH

OH

OCH3C.CH3CH2CH2OCH3D.

CH3CH2CH2OH4.按在水中的溶解度由大到小排列成序：A.B.

C.OCH3

OCH3D.CH2CH2CH2CH2

CH2CH2CH2CH2CH2CH2CH2CH2OH

OHOCH3OHCH2

CH

CH

CH2OH

OH

OH

OH5.按与氢溴酸进行SN1反应由快到慢排列成序：A.(CH3CH2)2CHOD.

O

E.B.

(CH3CH2)3CO

C.

O2N

F.

CH3CH2CH2OOCl

OB

＞A>F>D>E>CA.2OH

OH2OHB.3.按沸CH点由CH高

C到H

低排C列H

成C序H

：CH2

2OHOH

OCH3C.CH3CH2CH2OCH3D.

CH3CH2CH2OH4.按在水中的溶解度由大到小排列成序：A.B.

C.OCH3

OCH3D.CH2CH2CH2CH2

CH2CH2CH2CH2CH2CH2CH2CH2OH

OHOCH3OHCH2

CH

CH

CH2OH

OH

OH

OH5.按与氢溴酸进行SN1反应由快到慢排列成序：A.(CH3CH2)2CHOD.

O

E.B.

(CH3CH2)3CO

C.

O2N

F.

CH3CH2CH2OOCl

OB

＞A>F>D>E>CA.2OH

OH2OHB.3.按沸CH点由CH高

C到H

低排C列H

成C序H

：CH2

2OHOH

OCH3D.

CH3CH2CH2OH

A

＞

B>

D

＞

C4.按在水中的溶解度由大到小排列成序：C.CH3CH2CH2OCH3A.B.

C.OCH3

OCH3D.CH2CH2CH2CH2

CH2CH2CH2CH2CH2CH2CH2CH2OH

OHOCH3OHCH2

CH

CH

CH2OH

OH

OH

OH5.按与氢溴酸进行SN1反应由快到慢排列成序：A.(CH3CH2)2CHOD.

O

E.B.

(CH3CH2)3CO

C.

O2N

F.

CH3CH2CH2OOCl

OB

＞A>F>D>E>CA.2OH

OH2OHB.3.按沸CH点由CH高

C到H

低排C列H

成C序H

：CH2

2OHOH

OCH3D.

CH3CH2CH2OH

A

＞

B>

D

＞

C4.按在水中的溶解度由大到小排列成序：C.CH3CH2CH2OCH3A.B.

C.OCH3

OCH3D.CH2CH2CH2CH2

CH2CH2CH2CH2CH2CH2CH2CH2OH

OHOCH3OHCH2

CH

CH

CH2OH

OH

OH

OHD ＞

C ＞

A

＞

B5.按与氢溴酸进行SN1反应由快到慢排列成序：A.B.

O2N

CH2OHCH2OHC.

CH3O

CH2OH6.按酸催化脱水由易到难排列成序：A.CHCH3

B.

H2N

OHCHCH3

C.

O2NOH

CHCH3OH7.

下列化合物哪些能与2,4-二

肼反应，哪些能发生碘仿反应，哪些能发生银镜反应，哪些能发生自身羟醛缩合反应，哪些能发生Cannizzaro反应？A.

HCHO

B.

CH3CHO

C.CH3CHCH3OHF.

CH3COCH3D.

(CH3)3CCHOE.

CH3CH2CHCH2CH3OHA.B.

O2N

C

＞

ACH2OH

C.

CH3O>6.按酸催化脱水由B

易到难排列成序：CH2OH

CH2OHA.CHCH3

B.

H2N

OHCHCH3

C.

O2NOH

CHCH3OH7.

下列化合物哪些能与2,4-二

肼反应，哪些能发生碘仿反应，哪些能发生银镜反应，哪些能发生自身羟醛缩合反应，哪些能发生Cannizzaro反应？A.

HCHO

B.

CH3CHO

C.CH3CHCH3OHF.

CH3COCH3D.

(CH3)3CCHOE.

CH3CH2CHCH2CH3OHA.B.

O2N

C

＞

ACH2OH

C.

CH3O>6.按酸催化脱水由B

易到难排列成序：CH2OH

CH2OHCHCH3

B.

H2N

OHB

＞A.CHCH3

C.

O2NOH>

C

CHCH3OH7.

下列化合物哪些A能与2,4-二

肼反应，哪些能发生碘仿反应，哪些能发生银镜反应，哪些能发生自身羟醛缩合反应，哪些能发生Cannizzaro反应？A.

HCHO

B.

CH3CHO

C.CH3CHCH3OHF.

CH3COCH3D.

(CH3)3CCHOE.

CH3CH2CHCH2CH3OH能与2,4-二 肼反应的有：A、B、D、F。能发生碘仿反应的有：B、C、F。能发生银镜反应的有：A、B、D。能发生自身羟醛缩合反应的有：B、F。能发生Cannizzaro反应的有：A、D。8.按羰基活性由大到小排列成序：D.

CH3CHOE.OA.

(CH3)3CCC(CH3)3CHOOB.

CH3CCHOOC.

CH3CCH2CH39.用化学方法鉴别：CHOCH3

OH

CH2OHCOCH3O==O能与2,4-二 肼反应的有：A、B、D、F。能发生碘仿反应的有：B、C、F。能发生银镜反应的有：A、B、D。能发生自身羟醛缩合反应的有：B、F。能发生Cannizzaro反应的有：A、D。8.按羰基活性由大到小排列成序：D.

CH3CHOE.OA.

(CH3)3CCC(CH3)3CHOOB.

CH3CCHOOC.

CH3CCH2CH3B

＞

D

＞

E>

C＞

A9.用化学方法鉴别：CHOCH3

OH

CH2OHCOCH3O==O三、写出下列反应的反应历程CHOOHCH3

CH2OHCOCH3O=

=OABCDE2,4-二肼作

用(结晶)A

D

EBr2/H2O不作用A

D褪色E3

2Ag(NH

)

+不作用D沉淀(银白色)不作用B

C1

%FeCl3不作用C显色B1.下列化合物发生分子内的反应，试写出反应过程及产物，并标明构型。(1)C6H5H

OHH

BrCH3

CH3(2)C2H5HOHClH1.下列化合物在碱性条件下发生分子内的反应，试写出反应过程及产物，并标明构型。(1)C6H5H

OHH

BrCH3

CH3(2)C2H5HOHClH(1)CH3C6H5OH

SHH

R

Br3

HOHCH

H

BrC6H5C

H6

5OHBrH

CH3H

OHC

H6

5OBrH

CH3HCH3HOC6H5HSS(2)CH3C2H5HOR

HH

R

Cl3

C2H5HOHHCH

ClC

H2

5OHClCH3

HH

OHC

H2

5OClCH3

HHCH3OHC

H2

5HRS2.CH33C

CHOH

HBrCH3CH3Br(2)CH3C2H5HOR

HH

R

Cl3

C2H5HOHHCH

ClC

H2

5OHClCH3

HH

OHC

H2

5OClCH3

HHCH3OHC

H2

5HRS2.CH33C

CHOH

HBrCH3CH3BrCH33C

CHOHH+CH3C

CH3+OH2CH3CH3C

CH3H2O+CH3+

BrCH3CH3Br3.

OHCCH2CH2CH2CHCHOCH3

OHCHOCH3

OHCHOCH3CHOCH3CH2CH

CCH33.

OHCCH2CH2CH2CHCHOCH3CH2CH2CHOOH

OHCH2CHCHOCH2CH

CCH3O

HCH3CHOOHH2OHCH3CHOOH

△H2O4.HOCH3CH3OHH+CHOCH33

OHCHOCH3CHOCH3CH2CH

CCH33.

OHCCH2CH2CH2CHCHOCH3CH2CH2CHOOH

OHCH2CHCHOCH2CH

CCH3O

HCH3CHOOHH2OHCH3CHOOH

△H2O4.HOCH3CH3OHH+CHOCH33CH3OHCH3OHH+CH3OHCH3+OH2H2OCH3CH3OH+OCH3CH3CH3CH3+OH

O+HCH3CH3

H+四、

题1.以苯和C3以下的醇为原料CH2CH3：C6H5CH2CCH2CH2CH3OH四、

题OCH3CH3CH3CH3+OH

O+HCH3CH3

H+CH2CH3：C6H5CH2CCH2CH2CH3OH1.以苯和C3以下的醇为原料分析：CH2CH3C6H5CH2CH3CH2C=OC6H5CH2CCH2CH2CH3

CH3CH2CH2MgX

+OHC6H5CH2CH3CH2CH

OHC6H5CH2MgX+

CH3CH2CHO：CH3CH2CH2OHCrO3

-

C5H5NCH3CH2CHO

SOCl2Mg乙醚CH3CH2CH2MgClHCHO,HClZnCl22CH

ClMg乙醚gCl①

CH3CH2CHO3②

H

O+CH2CCH2CH3=O①

CH3CH2CH2MgCl②

H3O+3CH2CH3C6H5CH2CCH2CH2CHOH2.以乙烯为原料2－乙氧基－己烷。HCHO,HClZnCl22CH

ClMg乙醚gCl①

CH3CH2CHO3②

H

O+CH2CCH2CH3=O①

CH3CH2CH2MgCl②

H3O+C6H5CH2CCH2CH2CH3CH2CH3OH2－乙氧基－己烷。2.以乙烯为原料分析：CH3(CH2)3CHCH3①OCH2CH3②混

醚①CH3(CH2)3CHCH3

+

CH3CH2ONaCl3 2

3

3

3

2CH

(CH

)

CHCH

+

CH

CH

ClONaCH3(CH2)3CHCH3OH不可取(易消除)CH3(CH2)3CHCH3ONaCH3(CH2)3CH

=CH2CH3(CH2)3CH2CH2BrCH3(CH2)3CH2CH2OH②可取CH3(CH2)3CHCH3OH+CH3(CH2)3CH

=CH2

H2O,

H：CH2=CH2O2,

AgH2O,

H+OCH3CH2OH

SOCl2

Mg乙醚OH3O+CH3(CH2)3OHCH3(CH2)3OH

HBrMgO乙醚H3O+CH3(CH2)3CH2CH2OHHBr

NaOH2

5C

H

OH