有机化学综合复习题（附答案）

1

OHOH+

H2SO4H

(2).(CH)CC(CH)

(1).(CH3)3CCH2OH3232

HSONaBr,H2SO4

(3).24(4).OH

OH

OHHBrPCC

(5).(6).OH

CH2Cl2

CH

CH33

PBr3

(7).HOHO(1)C2H5MgBr

acetone(8).

CHCH()HO+

25323

CH3

OCHCHCH2OH

H5IO6

(9).(10).CH3

CH3

OH

CH3

HSO(1)O3

(11).24

CH3AB

H

(2)Zn,H2O

OH

2

1

CH2OHCH2OCH3CH2OCH3

CH2OHCH2OHCH2OCH3

b.p.197C125C84C

2AB

OHO

MnO2

(A)

MnO2

(B)O

OH

3ABAOHeBOH

a

OHOH

O

(A)(B)

O

↑

CH3OHOH

CH3

(1)OH(2)(3)(4)

OH

CH3OH

HOOH1

OH

→1

(1).C(CH)(2).(CH)CC(CH)(3).

65265232

OHOHOHOH

OHOH

↓AlCl3Fries

OCOCH3OHOH

AlCl3

COCH3

+

CS2

COCH3

1

2↓16↓

只

O

OHHBr

(1).CHCH2

CH3

(2).H2SO4

OH0C

OH

(3).H2SO4

O

OH

+

(4).H

OCHCHCH

22HBr

(5).

O

8RCOOCAr3RCOOCR3

CH3COOCPh3

9

O

COCHOCH3

10

CH3CH3

1)SOCl2

C6H5CH2CHCOOHC6H5CH2CHNH2

2)NH3

(+)

(S)-()

3)Br2,OH

2

RS

11

11(1)C7H13O2BrIR2850~2950cm3000cm

1

1740cmδHppm1.03H4.61H4.21H

1.36H2.12H

(2)AC12H14O3A

BC10H9O3NaBCC

C9H10OABC

12

CH2CH2Br

NaOH

(1).

N

O

H

(2).(CHCH)NH+CHC(CH)

322232

CH3

HNO/HSO(CHCO)O

324Fe/HCl32HNO3/H2SO4

(3).ABCD

CH3

+

H3O

NO2

NH2

NaNO2,HCl

(4).CH3CH2C(CH3)2

HO

NH22

+HN(CH)

(5).C6H5COCH3+HCHO32

CO2CH3

CHO

CH2+

CH3H3O

(6).++COAB

NHCHCO2

CHO22

CO2CH3

(7).-

N+OH

CH3

O

(8).+hv

CH3OCCHNN

O

H

N

(9).C6H6,(1)CH2CHCN

+AB

()HO,

22

COCH

(10).+225EtONa

CH3

CO2C2H5

(11).CH3NCO+EtOH3

NH2OH

HNO

(12).2

AB

NHNH

H+

(13).

(14).(H3C)2CNNC(CH3)2

CNCN

NaN3KOH

(15).CHCHCOClAB

652C

PCl5

(16).

N

OH

13

+

--

(1).(CH3)2CHCHCH3OH(2).(CH3CH2)3NCH2CH2COCH3OH

+N(CH3)3

++

(3).ClCHCHN(CH)OH-(4).CHCHN(CH)OH-

22322232

CHCH-CH2CH3

23O

N(CH)

+32

+

(5).PhCH2CHN(CH3)2(6).

-

CH3O

CH3

N(CH)OH-

+33

(7).

CH3

PhH

+

HN(CH)OH-H3CPh

(8).33(9).

HCH3

H3CH

+

PhN(CH3)2

O-

14

1A(C7H15N)B(C8H18NI)BAgOHC(C8H17N)C

AgOHD(C6H10)DH2E(C6H14)E

16ABCDE

2A(C4H9NO)AgOHB(C6H15NO2),BC(C6H13NO,C

AgOHD(C7H17NO2),DABCD

4

1

3A(C14H12NOCl)6mol样LHClB(C7H5O2Cl)C(C7H10NCl)BPCl3

NH3D(C7H6NOCl)NaOBrE(C6H6NCl)E5NaNO2/H2SO4

1

F(C6H6ClO)FFeCl3HNMRδ=7~8C

NaNO2/H2SO4GCHA~H

4A(C5H11N)ABC5H13N)B

ACC8H18NIC

D(C5H8)DE(C11H14O4)E3

A~ECD

CH3CH3

CH3Br

HCCl

HCHHCBr

(1)HOH3(2)

HCClHCBr

HBrHOH

CH3CH3

CH3CH3

CH3CHCHHH

325H

HBrHCH3

(3)(4)

Cl

HHClHC2H5C2H5

C2H5

CH3Br

HHHCH

(5)3CH3

CCCCCC(6)

H3CCH3H3CH

CH3C2H5

C2H5CH3

(7)

HBrBrH

HBrHBr

HH

(8)CH3H3CCH

H3C3

HH

16A(C6H10)B(C6H9Ag)A

C(C6H14)CBCARS

17

HHHHν

(1)(2)(3)

CH3CH3CH3CH3

5

CH3

(4)(5)HCH3

H

18C3H6(A)C3H6Cl2(B)C3H5Cl(C)(C)

C5H10(D)NBSC5H9Br(E)(E)C5H8(F)

(G)(A)(G)

1414

191CH3CH=CH2H2C=CHCH2Br

2HBr

aH2C=CHCH2CH3bCH3CH=CHCH3cH2C=CHCH=CH2

dCH3CH=CHCH=CH2eH2C=C(CH3)C(CH3)=CH2

3BrBrSN2

114214

4

112214313414

513

20

CH3

1

CHCOCH

33CH3CHCCH3

CH3OH

O

2

CH3CH=CH2HCCHCH3CH2CH3CCH2CH2CH2CH3

FCHCOCH,BrCHCHCOCHFCHC(CH)=CHCHCOCH

3232232323

4

CHO

21

O

(1)(A)HCN

CH3CHCH2CH3CH3CCH2CH3(B)

OH

OH_

H2O

(2)H3CCHO+CH3CHO(A)(B)

NaOH

(3)(CH3)3CCHO+HCHO(A)+(B)

O

(4)(A)

CH3CH2CCH3+H2NNHNO2

NO2

OOH

(5)CH3OHOC2H5MgBr

+CH3CCH3(A)(B)(C)

K2CO3HCl

6

CN

NHCl20%HCl

4(D)(E)

6CH3CH=CHCOC6H5+HCNA

7C6H5CHO+HOCH2CH2OHA

CH3

8C4H9LiCH3CH=CHC=O

PhP+CHCHBr(A)(B)(C)

332

9Zn—HgHCl

COCH3(A)

HCl

10O(A)

22

CHOOH

CH=CHCOCH2CH3

+CH3COCH2CH3

H2O

H2SO4

CHOCH=CCOCH3

+CH3COCH2CH3HOAc

CH3

O

(1).(2).(3).

(CH3)2CCHCH3CH3CC(CH3)3

Br

(4).CH(CH)CHBr(5).(6).CH(CH)CHO

3232325

CH

3CH3

(7).(8).antiomer

HBrOH+

C2H5

C2H5

CH3

7

1.OH

H3CCH3OO

CH

(9).(10).(11).3

CH3C(CH2)4CCH3A

CHCHCHCH

32CH3

CH3

BO

CH3

2.1O

2AB

MnO2

↑AB

H

OHO

(A)(B)O

O

3.

2↑1→

O

(1)(4)O

O

→.O

1

+

HH2O

C(C6H5)2C(C6H5)2C(C6H5)2

OHOH

OHOH2OH

CH

65C6H5

H+CH

C6H565O

CH

2↑OHO3

(2)(C6H5)2CCOCH3(3)

↓1100

2

16↓

2↓

只

OHOHOHO

+H+

CHCHH

(1).2CHCH3

CH3

CH38

+

(2).HH2O

OHOH2

H+

OHOH2

+

(3).HH2O

H+

OHOH

OCH2CHCH2CH2CHCH2+CH2CHCH3

(5).H

H

O

H+

CH3

O

CH

3OHOH

(6).BrOH

HOCCHCH2

H3CCCHCH2(CH3)2CCHCH2Br

CH3

CH3Br

O

+

H

(CH3)2CCHCH2Br

8AAL1

+O

+OH

Hslow+

CHC+CPh3

CH3COOCPh3CH3COCPh33OH

H2O

+

HOCPh3H2OCPh3

H+

9

+OH

O+

HCOCHOCH3

COCHOCH3

9

slow+H2O

CHOCH3CHOCH3

2

(SP)OH

+

(raceme)

CO2H

10Hofmann

OCHCHO

CHCHOC6H5CH2NH652

652SOCl23

CCCCCC

HNH

HOHHCl2

CH3CH3

CH3S

SS

C6H5CH2

Br,OH-

2CNH2

H

CH3

S

S

1111C7H13O2Br1C=CC=O

2IROHC=CH

3IR1740cm1A

41C=C

51HNMR

Br

OCH3

CH3CH2CHCCCH

O3

H

1HNMR1.02.14.24.61.3

(δppm(3H,t)(2H,m)(1H,t)(1H,m)(6H,d)

1121AC12H14O36

2DarzensClaisen

O-

NaNH2

CO+ClCH2COOC2H5CCHCOOC2H5

CH3H

C3Cl

OO

Cl--OH

CCHCOOC2H5CCHCOONa

CH3

CH3

+O

H3O

CCHCOOHCHCHO

ABCCH3CH3

OO

A.

CCHCOOC2H5B.CCHCOONa

CH3CH310

C.CHCHO

CH3

CH3CH3

12OH

(1).(3).

N(2).(CH3CH2)2NCH2C(CH3)2AB

NO

CH3CH32NH2

OH

CD

(4).(5).

CH3CH2C(CH3)2C6H5COCH2CH2N(CH3)2

NO2

NHCOCH3NHCOCH3

CH3CH3

NN

CO2CH3

(6).A(7).

BN

CH3

H3CO2C

O

OO

CN

N

(8).(9).

CHCO2CH3AB(11).CH3NHCO2Et