CHEM 201

Some practice
1.(30) Name or draw the following compounds where appropriate. Be sure to pay
attention to stereochemistry.

OCH2CH3

b)

a) (CH 3)2CHOC

CH
O

c) isopropyl vinyl ether

CO2H

d)

C6H5

CN(CH3)2
e)

OH

f)
C6H5

4.(15) Arrange the following in order of increasing (1=least or lowest or slowest..)

a) rate of hydrolysis in H3O+:

CH3CO2CH3 , CH3COCl , CH3CONH2 , (CH3CO)2O

b) reactivity toward electrophilic aromatic substitution:

O
CH

NO2

CH3

Cl

5.(50) Give the major products for the following reactions:

CH3
HCl, 125 oC

a) CH3

O
CH3

1) CH3CH2CH2CCl, AlCl 3

b)

2) H2, Pd on Carbon
HBr in ether

c)

O
CH

1) (CH3)2CHMgCl in ether

d)

2) H3O
O

NH2NH2, KOH
250oC

e)

f)

+ CH2=CHCH=CH2
OH

g)

h)
O

heat

(CH3)3SiCl, pyridine

OCH3

1) SO3, H2SO4
2) HNO 3, H2SO4
+
3) Dil. H 3O
1) HOCH2CH2OH, H

i)
O
j)

2) LiAlH 4
CHO 3) H3O+
CO2CH2CH3 1) NaOEt, EtOH
2) 1-bromobutane
+
3) H3O / heat

8.(30) Give reasonable mechanisms for the following reactions. Use only the reagents
provided and show all intermediates.

NO2

NO2
Cl2, FeCl3

a)

Cl

CH3
b)

CH3

H , H2O

CH3

+ H2O
CH3

OH

CH3

CH3
c)

HCl

Cl

9.(30) Give the reagents necessary to carry out the following transformations:

CH2

a)
CH

CH

Br

CO2CH3

b)
CH2CH3

O
c)
CH3
OH

OH