Question #47fbe

1 Answer
Jan 2, 2018

Here's what I get.

Explanation:

(a) 1-Chloro-3-methylcyclopentane with aqueous "NaOH"NaOH

This is an "S"_text(N)2SN2 substitution. The product is 3-methylcyclopentanol.

3-methylcyclopentanol3-methylcyclopentanol

(b) 2-Bromo-2-methylpentane with ethanolic "NaOH"NaOH

This is an "E2"E2 elimination. The major product is 2-methylpent-2-ene, and the minor product is 2-methylpent-1-ene.

E2E2

(c) Mechanism

The hydroxide ion reacts with ethanol to produce ethoxide ion in an equilibrium reaction.

"CH"_3"CH"_2"OH" + "OH"^"-" ⇌ "CH"_3"CH"_2"O"^"-" + "H"_2"O"CH3CH2OH+OH-CH3CH2O-+H2O

The ethoxide ion is a stronger base than "OH"^"-"OH-.

MechanismMechanism

(d) "We leave it as an exercise for the student" to compare and contrast the "S"_text(N)2SN2 and "E2"E2 mechanisms.