Question
How will you bring about the following conversion?
Ethanol to but-1-yne.
Ethanol to but-1-yne.
✓
Answer
Ethanol to but-1-yne.
$\text{CH}_3\text{CH}_2\text{OH}\xrightarrow{\text{SOCl}_2.\text{Pyridine}}\text{CH}_3\text{CH}_2\text{Cl}+\text{SO}_2+\text{HCl} \ \\ \text{Ethanol}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Chloroethane}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \\$
$\text{HC}\equiv\text{CH}+\text{NaNH}_2\xrightarrow{\text{Liq.NH}_3}\text{HC}\equiv\stackrel{{-}}{\hbox{C}}\stackrel{{+}}{\hbox{N}}\text{a}\ \\ \text{Ethyne}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Sodiumacetylide}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \\$
$\text{CH}_3\text{CH}_2-\text{Cl}+\text{HC}\equiv\stackrel{{-}}{\hbox{C}}\stackrel{{+}}{\hbox{N}}\text{a}\rightarrow\text{CH}_3\text{CH}_2\text{C}\equiv\text{CH}+\text{NaCl}\ \\ \text{Chloroethane}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{But-1-yne}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \\$
$\text{CH}_3\text{CH}_2\text{OH}\xrightarrow{\text{SOCl}_2.\text{Pyridine}}\text{CH}_3\text{CH}_2\text{Cl}+\text{SO}_2+\text{HCl} \ \\ \text{Ethanol}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Chloroethane}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \\$
$\text{HC}\equiv\text{CH}+\text{NaNH}_2\xrightarrow{\text{Liq.NH}_3}\text{HC}\equiv\stackrel{{-}}{\hbox{C}}\stackrel{{+}}{\hbox{N}}\text{a}\ \\ \text{Ethyne}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Sodiumacetylide}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \\$
$\text{CH}_3\text{CH}_2-\text{Cl}+\text{HC}\equiv\stackrel{{-}}{\hbox{C}}\stackrel{{+}}{\hbox{N}}\text{a}\rightarrow\text{CH}_3\text{CH}_2\text{C}\equiv\text{CH}+\text{NaCl}\ \\ \text{Chloroethane}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{But-1-yne}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \\$
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