Question 1:

1.O3 1.Br2,CH2Cl2
2.Zn,H2O 2.KOH,EtOH,to 1.BHR2,THF 1.NaOH,to 1.SOCl2
3.H2,Ni 3.NaNH2 (1:1) 2.H2O2,OH-,H2O 2.H2 excess, Ni 2.KCN
4.H2SO4,to 4.CH3Br 3.H3O+

1.LiAlH 4
2.H3O+ 1.HBr 1.Br2,hv
3.PCC 2.benzene,AlCl 3 2.AlCl3,to
4.Ph3P=C(CH3)2

Question 2:

O O 1.LiAlH 4
2.H3O+
3.PCC(excess)
4.OH-,to

Question 3:
1.HBr,ROOR OH
1.Br2,hv 1.C2H5Br, AlCl3
2.benzene,AlCl 3 1.Mg,ether HO
2.Li 2.Cl2,Fe
2.CH3CHO
3.CuI 3.H3O+
4.CH3CH2Br 4.PCC

1.Br2,hv
HO3S
2.KOH,EtOH,to
3.RCOOOH
4.H3O+

Question 4:
Cl
1. ,AlCl3 1.LiAlD4
1.Fe,HCl 1.CuCN 2.T3O+
2.NaOH,H2O 2.Br2,Fe 3.TBr
3.NaNO 2,HCl 3.H3O+,to 4.Mg excess
2.HNO3,H2SO4

1. O

2.DO18D

Question 5:
1.HBr 1.Cl2,Fe 1.PCC
1.Br2,hv 1.Na2CO3,H2O
2.Li 2.Mg,ether 2.HNO3,H2SO4
2.benzene,AlCl 3 2.CH3COCl,pyridine
3.CuI 3.CH3CH2CHO 3.Fe,HCl
4.CH3Br 4.H3O+

1.Br2,Fe 1.NaBH4
2.H3O+,to 1.NaNO2,HCl 2.H3O+
3.Na2CO3,H2O 2.HBr/CuBr 3.PBr3
Question 6:
Using benzene (C6H6), propene (CH3-CH=CH2), pyridine, DMF, Cl2, NaOH, NaCN, HCl, H2SO4, HNO3, H2O,
H2O2, N2H4, BH3, SOCl2, AlCl3, temperature. Produce this:
Cl
NO2 Know that there is no appearance of n-butylbenzene through the process

Question 7:
CH2CH3
H3C CH2CH2Cl NaOH(1:1)
Cl H DMF

Question 8:
1.BrMg-CH2-(CH2)3-CH2MgBr(1:1)
O
2.H3O+
3.PCC excess
O

Question 9:
1.HBr,ROOR 1.HBr,ROOR
2. 2.Li 1.Br2,hv
1.H2O,HgSO 4,H2SO4 OK ,to 3.CuI 2.Li
2.Ph3P=CHCH3 4.C2H5Br 3.CuI

1. 1.SOCl2, pyridine
Br 1.Mg,ether 2.Mg,ether
2.CH3CH2CHO 3.CH3CHO 1.SOCl2,pyridine
2.Br2,hv 3.H2O 2.KOH,EtOH,to
4.H3O+

Question 10:
Cl
1. ,FeCl3 1.Mg,ether
2.HCHO
1.Ph3P=CH2 3.H3O+ 1.NaBD4
2.HBr,ROOR 4.PCC 2.D3O+

O O
2.
O

FeCl3
Cl

Cl
Question 11:
Using buta-1,3-diene (CH2=CH-CH=CH2), prop-2-enal (CH2=CH-CHO), DMF, C2H5OC2H5, pyridine, H2, Mg,
NaOH, NaOCH3, (C2H5)3COK, HBr, H2SO4, H2O, PCC, PBr3, temperature. Produce this:

Question 12:
1.CH2=CHCH2Br (excess),K2CO3
2.HBr,peroxide
OCH3 3.Mg,THF
4.CO2
5.H3O+
HO

Question 13:
Using benzene (C6H6), propane (C3H8), DMF, C2H5OC2H5, Fe, Mg, Br2, NaOH, HCl, HBr, H2SO4, HNO3, H2O,
H2O2, CO2, temperature, light. Produce this:

O O

Question 14: Cl 1.Zn(Hg),HCl

2.H2SO4,to O O
O 1.FeCl3, 3.NaOH solid, to
13
4.H3O+ H2C O18 C13H2

2.FeCl3, O O

Question 15:
Cl 1.Mg,ether
1.NaBH4 2.HCHO
O 1.FeCl3, 2.H3O+ 1.NaBD4
3.H3O+
3.HBr 4.PCC 2.T3O+

2.FeCl3, O O

1.SOCl2,pyridine
2.Mg,ether

3. OT
Question 16:

H3C C2H5 CH3ONa

CH(CH3)2 to
H Br

Question 17: 1.Br2,CH2Cl2

1.SOCl2,pyridine 2.NaNH2 excess,to
1.KOH,EtOH,to 1.PCC 2. 3.HCHO
Cl
2.CH2=CH-CHO,to 2.CH3MgBr OK ,to 4.H3O+
3.H2 excess,Ni 3.H3O+ 5.PCC

1.CH3CH2NH2,H+
2.H2 excess,Ni
3.CH3I excess

Question 18:
H3C H 1.SOCl2,pyridine

2.DMSO,
CH3
H3CH2C OH H3CH2CH2CH2C H
ONa

Question 19:

1.H2 excess,Ni
NO2 2.CH3COCl excess
3.LiAlH 4 excess
O 4.H2O

Question 20:

Cl
CH3OH,SN1
 Question 21:

1.C2H5ONa,to
H3CH2 2.BH3,THF
H CH3 3.H2O2,NaOH,H2O
Br

Question 22:
Using nitrobenzene (C6H5NO2), CH3COCl, OH-CH2-CH2-OH, C2H5OC2H5, Zn, Mg, HCl, NaOH, NaNO2, H2SO4,
H2O, NaBH4, AlCl3, CuCl, CO2, temperature. Produce this:
COOH

HO

Question 23:

H3CO
1.H3O+
O 2.PCC excess
3.C2H5MgBr excess,THF
O 4.H3O+

H3CO

Question 24: 1.NaH

Cl
Cl 1.LiAlD 4 2.
1.FeCl3, 1.Cl2,FeCl3 2.H3O+
2.Zn(Hg),HCl 3.HBr Cl
3.Mg,ether 4.KCN
4.CO2 5.H3O+
2.FeCl3, O O
5.H3O+ 6.LiAlT 4
O 7.D3O+

Question 25:

Using C6H5Cl, DMF, H2, Pd, NaOH, NaNO2, NaOCH3, CH3OH, H2O, H2SO4, HNO3, H3PO2, temperature. Produce
this:

Cl

N
N O
 MY ANSWER

Question 1: Question 2:
O

18
DO

D2C

Question 3: Question 4:
O
HO OH
O18D

Br Br
Question 5:

Br

1.BH3
2.H2O2,OH-,H2O
3.SOCl2,pyridine
4.NaCN,DMF 1.SOCl2,pyridine
Question 6: 5.H3O+ 2.benzene,AlCl3
COOH
O

1.HNO3,H2SO4 Cl
2.N2H4,OH- NO2
3.Cl2,AlCl3

CH2CH3 CHO
H3C CH2CH2Cl
Question 7: H OH Question 8: OH

H
Question 9: Question 10: Cl O

O D
Question 11:

CH2=CH-CHO,to CHO
H2 excess,Ni CH2OH PCC CHO

1.PBr 3,pyridine
2.Mg,ether

CHO
1.
CH2MgBr
OH
2.H3O+

1.PBr3,pyridine O
13
2.(C2H5)3COK,to H2C O

Question 14: O

O CHDT
OCH3
Question 15:
Question 12:
O

HOOC

Question 13:

HIC HIC :'D

Br

1.H2SO4,to
1.Mg,ether
2.Br2,Fe
Br 2.CO2 COOCH2CH2CH3
3.NaOH,to
3.H3O+
4.CH3CH2CH2Br
4.CH3CH2CH2OH,H3O+
O O
 H3C C2H5
N+I-
Question 16: Question 17:
C6H5 CH(CH3)2

H H
H3C N
Question 19:
Question 18:
HOH2C
H
H3CH2C O
CH2CH2CH2CH3
CH3

Question 20:
H3CO OCH3

OH HO
Question 21: C2H5 C2H5
H CH3 H3C H

O
NO2
1.Zn,HCl
HN 1.H3O+ COOH
2.NaOH
Question 22: 3.CH3COCl 2.NaNO2,HCl
4.CH3COCl,AlCl3 3.CuCl,to
4.Mg,ether
5.CO2
6.H3O+ O
O
COOH
1.NaBH4
2.H3O+
Cl

OH
Question 24:
CD2CT2OCH2

H3CO
O

Question 23: O

H3CO O
Question 25:

Cl
1.HNO3,H2SO4
O 1.NaNO2,H2SO4,273K O
2.NaOCH3,DMF
3.H2,Pd 2.H3PO2

NH2

1.HNO3,H2SO4
2.H2,Pd
3.H2SO4,NaNO2,273K

Cl
O
Cl

N
N O
N2+HSO4-