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20042005

1 Multiple Choices ( 15 , 15 )
1 1 (0132)
Cl
NO2

(A)

,
:
+
NaHCO3
Cl

(B)
HO

NO2

Cl

OH

(C)
NO2

(D)
NO2

NO2
OH

OH

2 1 (9305)

OH

OH
A

CH3CH2OH

CH3OH

NO2

D
NO2

3 1 (7629)

NH2

(A)

NH3

(B)

Cl
(C)

NH2

NH2

(D)

4 1 (6791)
pKa

Cl

SO3H

SO3H

SO3H
NH2

SO3H
D

OH
Cl

NO2

5 1 (7729)
:
(A) ,
(B) ,
(C) ,
(D) ,
6 1 (0142)
90 C HNO3, H2SO4 ,:
(A) o-
(B) m-
(C) p-
(D)
71 (9307)

OH
A

CH3

OH

CH2

CH3

CH

OH
C

CH3

CHCH2OH

CH

CH3

CH

CH2

OH
CH
OH

8 1 (7767)
,
CH2
(A) CH3CH2C

(B) CH3CH2CNH2

CH

(C)

OH

9 1 (0602)
Ph3P :
(A)
(B)

(D)

OR

(C)

(D)

10 1 (4080)
, SN
(A ) C H 3 S N a

C H 3C l

(C H 3 )2 S
CH

(B ) C H 3 C H 2 O H
(C )

CH

CH

(D )

(C H 3 )2 C

B r2

C C l4

CH

H 2O

2 +

C H B r2C H B r2
OH

H 3C
+

N aCl

HCN
H 3C

C
2 CN

11 1 (0295)
(I), (II), (III), (IV):
(A) I>II>III>IV (B) II>III>I>IV (C) III>II>I>IV
(D) IV>I>III>II
12 13 1 (7480)

HO N
CH3

CH3 H2SO4

NH2

CH3

NH2
O
C

CH3
D

NH

CH3

14 1 (8051)
?
(A)

(B)
+

N
O

(D)

(C)

15 1 (0226)
(CH3)2C=CH2,?
(A) (CH3)2CHCH2OH

(B) (CH3)3COH

(C) CH3CH2CHCH3

(D) CH3CH2CH2CH2OH

OH

Name the following compounds or draw the structures of the compound.10 10

C6H5

(CH3)2CHNH2

3. O2N

COOH

CH3
C C

CH3

COCH2CH3

COCH2CH3

4.

COOH
5.

HO

6. cyclohexanone oxime

OH
OH

7. 3,5-dimethoxybenzaldehyde

9. ethyl acetoacetate

8, N, N-dimethylformamide

10. aspirin

. Predict the main products of the following reactions30 30

1.
OH

Br2

2.
CH2CH3
h

Cl2

3.
H

H3 C

N+(CH3)3
H

4.
CH3
O

HN

SO3H

5.

OH-

OH
Cl

Na2Cr2O7
H2SO4

6.
O

_
CHCH2CN

Ph3P+

7.
N

OH

H2SO4

CH3

8.
CH3
CH3C

CHCH3

HBr

CH2

9.

H2SO4 PhCO3H H2O/H+

OH
10.

OH

H2SO4

CH3

HCOOOH

11

CH3

Hg(OAc)2 NaBD4
H2O
HO-

12.

CH3CH2C

CH

B 2H 6
THF

H2O2
HO-

13.
H

CO O Et
?

CO O Et

14.
CH2CHBrCH2CH3

15.

Et C

CH

KOH / ROH

(1 ) N a

(2 ) E tB r
(3 ) H 2 /L in d la r

?
5

HBr
ROOR

16.
CH2COCH3

NaOCH3

CH2COOCH3 CH3OH

17.

NaOH

PhCHO + CH3COPh
18.
O

COOCH3

NaOCH3
CH3CH2CH2Br

19.

Br2 , NaOH

CH3CH2CH2CH2CH2CONH2
20.
O
+

HN(C2H5)2

H2/Ni

21

Mg

2 CH3COCH3

H2O

1, Cl2, NaOH
+
2, H3O

PhH

22.

Cl
Cl2
FeCl3

Fe , HCl

CH3CH2COCl

NO2
23.
H3C

COOH

SOCl2

H2
Pd _BaSO4

24.

NBS
CCl4

1) HCHO
+
2) H3O

Mg
ether

25.
Cl
CH2(COOEt)2 NaOH

CHO

26.

CH3
+

CH3CH2N CH2CH2CH2CH3 OH
CH3

?
6

27.
CH2(COOC2H5)2 +

28.

N
H

NO2
CH3ONa / CH3OH

Cl
Cl

29.
O
NH

PhCH2Br

KOH(s)

1,H3O+
2,OH

30.
O
CO2Me

1.NaBH4
+

2.H / H2O

. Show how you would accomplish the following Synthesis in good yields5 20

NHCOCH3
1.

NO2

2synthesize the title compound by using propene as only carbon source

CH3
CH2

CHCH2

O CCH2CH2CH3
CH3

CH2CH3
3

CH2NH2

4
OH
H3C

5.
O
COOC2H5
COOC2H5

, CH2=CHCH2Br

 The following road-map problem centers on the structure and properties of A, a key
intermediate in these reactions. Give structures for compounds A through J. (10 )
OH
H

NaBH4

H+
I
warm gently

(1) J
(2)H3O+

(1) CH3MgI
(2) H3O+

OH
CH2OH

PCC
(excess)

OH OH(1 equiv) Tollens reagent

A
D
TsOH
dil chromic acid
PhNHNH2
(excess)
dil H2SO4
C

Zn(Hg)
HCl

A C8H12
BC8H18A CC8H14
DC8H14 A-D (5 )
.

. Propose a mechanism for the following reactions10

1.

AgNO3, H2O/CH3CH2OH
OH

CH2I

2.

CH2(COOEt)2

1, NaOEt
+
2, H3O

10