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Alcohols as Nucleophiles and Electrophiles

Which of the ...

Question

Which of the following is the proper method to prepare n-hexane from n-propyl alcohol?
$C H_{3} C H_{2} C H_{2} O H X - \to C H_{3} C H_{2} C H_{2} B r Y \to C H_{3} (C H_{2})_{4} C H_{3}$

(X) \to H B r, (Y) \to H C N

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(X) \to H B r, (Y) \to N a, e t h e r

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(X) \to B r_{2}, (Y) \to C H_{3} C N

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(X) \to B r_{2}, (Y) \to K M n O_{4}

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Solution

The correct option is D $(X) \to H B r, (Y) \to N a, e t h e r$
To prepare n-hexane from n-propyl alcohol:
$C H_{3} C H_{2} C H_{2} O H X - \to C H_{3} C H_{2} C H_{2} B r Y \to C H_{3} (C H_{2})_{4} C H_{3}$
Step 1: is a nucleophilic substitution reaction of $O H$ by $B r$ . This can be done by $H B r$
Step 2: this reaction is $R X \to R - R$ . It is the Wurtz Reaction in the presence of $N a$ and dry ether
Thus the reaction has $(X) = H B r, (Y) = N a, e t h e r$
$C H_{3} C H_{2} C H_{2} O H H B r - -- \to C H_{3} C H_{2} C H_{2} B r N a / e t h e r - ---- \to C H_{3} (C H_{2})_{4} C H_{3} + 2 N a B r$

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