EXERCISE 9

ELIMINATION REACTIONS

1. Show the E1 mechanism for the following reactions and then name the
products obtained.
(a) 2-iodo-2-methylpropane and OH−
(b) 2-chloropropane and cyanide ion (CN−)
(c) 2-fluoro-2,3-dimetilbutana and methoxide ion (CH3O−)

2. Show the E2 mechanism for the following reactions and then name the
products obtained.
(a) Iodoethane and OH−
(b) 3-chlorohexane and OH−
(c) 2-bromobutane and OH−

3. Compare the reaction between SN1 and E1 and complete the table below.

Characteristic SN1 E1

Similarities

Differences

4. Complete the table below.

Reactions
tems
E1 E2

No. of step/s ?
Formation of the
carbocation/transition
state ?
Base attack ?
Product?
5. Write (✓ ) for a TRUE statements and (  ) for a WRONG statements.

No. Statement Answer

The E2 is a second order reaction.

a.
The E2 involves two steps.
b.
c. The E1 tends to occur in primary carbocation.
The rate of E1 reaction is depends on the
d.
concentration of reagent used only.
Nucleophile attack alpha carbon to form an alkene.
e.
The first step for E2 reaction ia a formation of the
f. carbocation.

The elimination reaction is competitive with

g.
nucleophilic substitution reaction.
The product of the elimination reaction is depends
on the nucleophile used. If OH− is used, alcohol is
h.
produced and so as for cyanide ion, nitrile
compound is produced.
The product of E2 reaction is the formation of
i. multiple bond.

For E2 reaction, base is used to attract proton from

carbon, and at the same time halide ion is removed
j.
and a double bond is formed.

"I'm always doing things I

can't do. That's how I get
to do them"
- Pablo Picasso -