Question
An alkyl bromide (X) react with sodium metal dissolved in anhydrous ether to form 4, 5-diethyl octane. Identify 'X'.

Answer

$2\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{CH}-\text{CH}_2-\text{CH}_3+2\text{Na}\xrightarrow[\text{Ether}]{\text{Anhydrous}}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Cl}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ _{3-\text{chloro hexane}}\\{\stackrel{{1}}{\ \ \ \hbox{ CH}_3}}-{\stackrel{{2}}{\ \ \ \hbox{ CH}_2}}-{\stackrel{{3}}{\ \ \ \hbox{ CH}_2}}-{\stackrel{{4}}{\ \ \ \hbox{ CH}}}-{\stackrel{{5}}{\ \ \ \hbox{ CH}}}-{\stackrel{{6}}{\ \ \ \hbox{ CH}}}_2-{\stackrel{{7}}{\ \ \ \hbox{ CH}}}_2-{\stackrel{{8}}{\ \ \ \hbox{ CH}}}_3\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ | \ \ \ \ \ \ \ \ \ \ \ \ \ \ |\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{C}_2\text{H}_5\ \ \ \ \ \ \text{C}_2\text{H}_5\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ _{4,\ 5-\text{Diethyl octane}}$

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