Question
How the following conversions can be carried out?
Ethanol to But-2-yne.

Answer

$\text{CH}_3\text{CH}_2\text{OH}\xrightarrow[-\text{SO}_2,\text{ -HCl}]{\text{SOCl}_2,\text{ Pyridine}}\text{CH}_3\text{CH}_2\text{Cl}\\ \ \ \ \ ^\text{(ethanol)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ ^\text{(chlroethane)}$$\text{CH}\equiv\text{CH}+\text{NaNH}_2\xrightarrow[196\text{K}]{\text{liq. NH}_3}\text{HC}\equiv\text{C}^-\text{Na}^+\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ ^{(\text{sodium acetylide})}$
$\text{CH}_3\text{CH}_2-\text{Cl}+\text{HC}\equiv\text{C}^-\text{Na}^+\rightarrow\text{CH}_3\text{CH}_2-\text{C}\equiv\text{CH}\\ \ \ \ \ ^{(\text{chloroethane})}\ \ \ \ \ \ ^{\text{(sodium }}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ ^{(\text{But-1-yne})+\text{NaCl}}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ ^{\text{acetylide)}}$

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