作業(yè)1H

3C（產(chǎn)物用Newman投影式表示）HBrH+C

2

H

5BrCH3CH31)H

3CHCHH3Br2（產(chǎn)物用Fischer投影式表示）HBrCHBrH3+BrHCHHBr33H

CBrHHBrC

2H

52)H

3

CHHC

2

H

5Br2δ

δBr

Br3H

CHBraHC

2H

5bBraBrH

3

CHBrbHC

H2

5?H

3CHBrBrHC

2H

5H

3

CHC

2H

5HBr2（產(chǎn)物用NewmanC

2H

5投影式表示）H

3

CBrH+HHHBrCH3C

2

H

5BrBrδ

δBr

Br3H

CHBrabC

2H

5HBraBrH

3CHBrbC

2H

5H?H

3

CHBrBrC

H2

5H3)找出至少3種鹵取代藥物作業(yè)21）C

2H

5HOCH3濃HBr加熱＋2）CHHH3OHBrCH3濃HBr＋??設(shè)計(jì)從苯到1-溴-4-碘苯的合成路線。提示：反應(yīng)需要多步完成，如硝化、還原、鹵化或重氮化等反應(yīng)BrI1）C

2H

5BrCH3+C

2H

5BrCH32）CH3HHBrBrCH3+CHBrH3HBrCH33)路線一：NO2HNO3H

2SO

4Fe

+

HClNH2(CH

3CO)

2ONHCOCH3NHCOCH33HNOH

2

SO4NO2Fe,

HClNHCOCH3NaNO2,濃HClNHCOCH3NH2N

2

ClN

2

ClNaNO2,濃HClKIINHCOCH3CuBrH

2O/OHNH2BrBrBrBr3）路線二：Br3HNOH

2SO4NO2Fe,

HClNH2NBS,

DMFNaNO2

,濃HClBrNH2N

2

ClIKIBr作業(yè)3一、完成以下反應(yīng)方程式1)OSnCl

4CH

2Cl2,回流Cl2)OH+NO2KOH/DMSO90

℃BrBr3)BrNH3Cl4)NO2+NH2THF50

℃,

20h二、由丙二酸二乙酯及C

3或C

3以下有機(jī)原料合成COOC2H

5COOC2H

5COOH三、設(shè)計(jì)從苯到苯甲酰氯的合成路線COCl答案一、完成以下反應(yīng)方程式1)OSnCl

4CH

2

Cl2

,回流OHCl2)OH+NO2KOH/DMSO90

℃ONO2BrBr3)BrNH3N+H

2NNH2H

2NCl4)NO2+NH2THF50

℃,

20hO

2NHN二、由丙二酸二乙酯及C

3或C

3以下有機(jī)原料合成2CH

(COOEt)2+

BrCH222CH

CH

BrH2O/H

+???-?CO

22

NaOC2H

5C(COOEt)2COOH三、設(shè)計(jì)從苯到苯甲酰氯的合成路線?路線1+COClCOClAlCl3COCl?路線2+

CH

2

O +

HClZnCl

260

℃OHKMnO4AlCl3r.tAlCl3r.tCOOHSOCl2COClCl+OAlCl3r.t+H

2C

CH2+CH3Cl?路線3O+ClAlCl3ONa

2Cr

2

O

7/H2

OCOOHSOCl2COCl?路線4AlCl3/CuCl+

CO

+

HClCHO

KMnODMF/POCl34/CH

3

COOH/H

2Or.tCOOHSOCl2COCl作業(yè)41.以丙胺、C5或C6以下為原料，經(jīng)Dieckmann縮合反應(yīng)制備N-丙基-1-哌啶酮。NH

2ON2.以苯酚、C4及以下為原料，合成如下化合物OHOH

3CO3.以苯為原料合成如下化合物CH

2ClCl4.以甲苯、丙二酸二乙酯等為原料合成如下化合物

(提示：需要經(jīng)過2次活性亞甲基的C-酰化)CH

3CH

2CH

3H

3CO答案1.NH2+COOCH31,4-二氧六環(huán)NCOOCHCOOCH33CH3ONa/甲苯COOCH3HCl,加熱NONO2.HO(CH

3)2SO43H

COOOO

,

AlCl3H

3COCOOHOZn-Hg/HClH

3

COCOOHOSOCl

2H

3COCOClAlCl3H

3CO3.+CO+HClAlCl3/CuClCHOCl2/FeClCHOGattermann-Koch

反應(yīng)LiAlH

4ClCH

2OHSOCl2ClCH

2ClorZn-Hg/HClClCH3Cl2hvClCH

2Cl??H

3C+2CH

O+HClZnCl2H

3CCH

2

ClCOOC2

H

5COOC2

H

5H

3

CC

2H

5

ONaCH

2ClH

3CCH

2CH(COOC2H

5

)22

5C

H

BrC

2H

5ONaSOCl

2H

3CCH

2C(COOC2

H

5

)2C

H2

5H

2O/H,

-CO2H

3CCH

2

CHCOOHC

H2

5C

2

H

53H

C2CH

CHCOClC

2

H

5AlCl33H

CO作業(yè)5及答案一、完成以下反應(yīng)方程式1.EtOAc+O3Et2

O

BF

3,PhCH-10℃主要EtOAcCHO+EtOHC少量OAcOSiMe32.+OOSiMe3[4+2]+CHO主要OSiMe3CHO少量CHO3.NHCO

2

Et+O110℃[4+2]CHONHCO

2

Et主要O4.H

3

COMe

2NH

HClHCHO/Na

2CO3H

3COONMe2MeI/NaHCO3Et2OH

3

CO+NHCO

2Et少量O5.H

3

COH

3

COCHO+PPh3H

3COH

3COO6.O+CHONaOH2H

OOO作業(yè)6及答案一、解釋以下Wagner-Meerwein重排反應(yīng)的機(jī)理3PhHCH

OTsPh

C

CHCH3*CH3CH2CH

3Ph

C

CH*

CH

3HH

3

C

CC*Ph3CH CH

3*C

CH33Ph

CCH

3

CH+H

3

C

C

C*

PhCH

3

CH3CH3Ph

C3OTs×C

CHHCH3-

OTsCH3×HPh

CCH3-

HC

CH3CH3Ph×C3C

CHHCH3-

HCH3PhH

3

CCC

CH×3HCH

3CH3-

H×Ph

C3C

CHHCH3CH

3Ph

CC

CH×3CH3×Ph

CCH3C

CHH2r(CH

2)9C

作CHN

業(yè)2O7及答案Br(CH

2

)9CH2CONH2NH

3.H2O/AgNO3N2一、解釋反應(yīng)的機(jī)理1）