Organic chemistry: Work sheet 1

1. Which alkyl halide would you expect to react more rapidly by an SN2 mechanism? Explain
your answer.

2. Which SN1 reaction of each pair would you expect to take place more rapidly? Explain your
answer.

a) 1) + H2O + HCl
Cl OH

2) + H2O + HCl
Cl OH

b) 1) (2.0 M) + EtO- (1.0 M) EtOH + Cl-

Cl OEt

2)
Cl
(1.0 M)
+ EtO- (1.0 M) EtOH + Cl-
OEt

1) (1.0 M) + EtO- EtOH

c) + Cl-
Cl (1.0 M) OEt

2)
Cl
(1.0 M)
+ EtO- (2.0 M) EtOH + Cl-
OEt
3. Each of the following alcohols has been subjected to acid catalyzed dehydration and yields a
mixture of two isomeric alkenes. Identify the two alkenes in each case, and predict which
one is the major product on the basis of the Zaitsev rule.
OH
A) (CH3)2CCH(CH3)2 B)
OH
H

4. Outline efficient syntheses of each of the following alkynes from acetylene and any necessary
organic or inorganic reagents:
A) 1-Heptyne B) 2-Heptyne

1
5. Arrange with increasing order for the following cation in each set.

6. Complete the equations for the following reactions. Show all organic products – if two or
more products form, indicate the major product. Indicate proper stereochemistry where
necessary.

a. O3
(CH3)2S

b. HBr

CH3
c. H3O+

d. H2SO4
OH

e. POCl3
OH Pyridine

HBr
f. O

g. BH3, THF
H2O

2
h. HBr
ROOR

i. 1)BH3
2)H2O2

j. 1. O3
2. H2O

CH3
k. OSO4
H2O2

Br CH3

(CH3)3CO-K+
l.
(CH3)3COH

Br
m Zn
Br CH3COOH

7. Give the missing reagents and structures.

1
a. 2
Br

1 2 OH
b. Br

OH Br
c. 1 2 3
OH
d.
1
CH3C CH CH3C CCH2CH2CH2CH2CH3
2

8. Propose a mechanism for each of the following reactions:

a) HO Br
Br2
+ HBr
O

Cl
b) EtOH
Heat
3
 Br
c) HBr

OH
d) H2O

9. Provide the reagents necessary to complete the following transformation. The synthesis may
involve more than one step.
Br
OH
?

OH