Question:

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

Updated On: Apr 15, 2024
  • Polyvinyl alcohol
  • Divinyl ether
  • Dimethyl ether
  • Methyl vinyl ether
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The Correct Option is D

Solution and Explanation

When acetylene is passed into methanol at $160-200^�C$ in the presence of a small amount $(1-2\%)$ of potassium methoxide and under pressure just high enough to prevent boiling, methyl vinyl ether is formed.
The mechanism is believed to involve nucleophildic attack in the first step.
$\ce{HC$\equiv$ CH + CH3 O^-->C^-H=CH OCH3->[CH_3OH]CH2=}$ $\underset{\text{Methyl vinyl ether}}{\ce{CHO CH3 + CH3O�}}$
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Concepts Used:

Alkynes

In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon-carbon triple bond. Alkynes are an organic molecule that contains triple bonds between the carbon atoms. Its general formula is CnH2n-2. They are also known as acetylenes. In this article, we will deal with the structure of alkynes.

Isomerism in Alkynes:

Alkynes show three types of isomerism

  1. Chain isomerism - Due to the different arrangement of carbon atoms in the chain that is straight chain or branched.
  2. Position isomerism - Due to the difference in the location of the triple bond.
  3. Functional isomerism - Isomeric with alkadienes both being represented by the general formula CnH2n-1. 

Properties of Alkynes:

Physical Properties:

  • Non-polar, unsaturated hydrocarbons.
  • Highly soluble in organic and non-polar solvents and slightly soluble in polar solvents.
  • High boiling point, in comparison to other hydrocarbons.
  • Release a high amount of energy due to the repulsion of electrons in a reaction.
  • More acidic than alkanes and alkenes due to SP hybridization.

Chemical Properties:

  • Hydrogenation - Alkynes undergoes two types of hydrogenation reactions. Complete hydrogenation (in presence of Pd-C/ H2) and partial hydrogenation (in presence of Linder’s catalyst/H2).
  • Act as a strong nucleophile by converting into acetylide. 
  • React with BH3 and undergo hydroboration reactions to form aldehydes and ketones.
  • Undergo halogenation reactions in the presence of different halogenating agents by different mechanisms and forms haloalkanes.