First slide

Alkynes

Question

When acetylene is passed into methanol at 160-200°C in the presence of a small amount of potassium methoxide and under pressure, the following is formed:

Moderate

A

Divinyl ether
B

Dimethyl ether
C

Polyvinyl alcohol
D

Methyl vinyl ether

Solution

When acetylene is passed into methanol at 160°00 -200°C in the presence of a small amount(I-2%) of potassium methoxide and under pressure just high enough to prevent boiling, methyl vinyl ether is formed.The mechanism is believed to involve nucleophilic attack in the first step.
$HC \equiv CH + {CH}_{3} O^{⊖} \to C^{⊖} H = {CHOCH}_{3} \overset{{CH}_{3} OH}{⟶} {CH}_{2} = {CH}_{2} {OCH}_{3} + {CH}_{3} O^{⊖} Methyl vinyl ether$

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