Question #47fbe

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Answer 1 · 2018-01-02T21:21:05

Here's what I get.

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

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

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 $"OH"^"-"$ .

Mechanism

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