Question

Question #47fbe

Answer 1

Here's what I get.

Explanation:

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

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

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

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

(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"`

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

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