BIOL1026: Workshop 1

Lectures 1 and 2: Nucleophilic Substitution and Elimination

1. For each of the following sets of substrates and reagents, the reaction type is given. For
each reaction give a detailed mechanism and identify the structure of the product(s)
formed (4p each).
+

EE--odicT
+
5 5
⑦
=

n=
0.
- N

i 22 0
-

InJan
&
--.. ·

~5 Ej- 0- -
m

6.

NoixTnOsn N) +is

-> N
·

Ms
f

-
<-.. ron

2. The following substitution reaction of benzyl chloride (A) takes place via an SN1
mechanism:

La

(i) Provide a detailed mechanism for the reaction (3p).

(ii) Primary alkyl halides (one other substituent on the carbon bearing the leaving
group) do not usually undergo SN1 substitution. Suggest why SN1 substitution of
A does take place, although it is a primary alkyl halide (2p).

1sO

+
-

Aa
a

s
+

Interme die
carbocation
3. The following reaction proceeds via E2 elimination, to give a single alkene product
isomer. Deduce the structure of the product and assign its configuration (E or Z) (5p).

·.

&

--a
↑ H
*
Δ X 2 isomer

4. Deduce which is the product of the following E2 reaction. Justify your answer by using a
detailed mechanism (5p).

pom Nat Br
meanme
X
+
Ma0

...
recourse e

->
mainme
V +MaO
OR

+NaBr
V