Question
$\text{Pent-1-yne}\xrightarrow[(\text{ii})\ \text{CH}_3-\text{I}]{(\text{i})\ \text{NaNH}_2/\text{NH}_3}\text{A}\xrightarrow[\text{Lindlar's catalyst}]{\text{H}_2}\text{B}\xrightarrow{\text{Br}_2}\text{‘C’}$Identify A, B and C compounds and give their reactions.

Answer

$\text{HC}\equiv\text{C}-\text{CH}_2-\text{CH}_3\xrightarrow[(\text{i})\ \text{CH}_3-\text{I}]{(\text{i})\ \text{NaNH}_2/\text{NH}_3}\\\text{CH}_3-\text{C}\equiv\text{C}-\text{CH}_2-\text{CH}_2-\text{CH}_3\xrightarrow[\text{H}_2]{\text{Lindlar's catalyst}}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{‘A’}$
$\text{CH}_3-\text{CH}=\text{CH}-\text{CH}_2-\text{CH}_2-\text{CH}_3\xrightarrow{\text{Br}_2}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{‘B’}\\\text{CH}_3-\text{CH}-\text{CH}-\text{CH}_2-\text{CH}_2-\text{CH}_3\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\ \ \ \ \ \ \ \ \ |\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Br}\ \ \ \ \ \ \text{Br}\\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{‘C’}$

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