Question:medium

Identify substrate 'S' in the following reaction.
\(\text{S}\overset{\text{Na / dry ether}\,}{\rightarrow }\) 3, 4 - diethyl - 3, 4 - dimethyl hexane

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Wurtz joins two alkyl groups. Split the product in half to find the alkyl halide.
Updated On: Oct 1, 2026
  • 3 - chloro - 2 - methylpentane
  • 2 - chloro - 3 - methylpentane
  • 3 - chloro - 3 - methylpentane
  • 2 - chloro - 2 - methylpentane
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The Correct Option is C

Solution and Explanation

Step 1: Cut the product in two:
Draw 3,4-diethyl-3,4-dimethylhexane. The two quaternary carbons C3 and C4 are joined to each other. Each also bears a methyl, an ethyl branch and a chain end that is an ethyl.

Step 2: Name the fragment:
Each fragment is a carbon with substituents $-\text{CH}_3$, $-\text{C}_2\text{H}_5$, $-\text{C}_2\text{H}_5$. The parent is pentane with the carbon in the middle, position 3, so the fragment is a 3-methylpentan-3-yl group.

Step 3: Add the halogen:
The tertiary chloride is $\text{(C}_2\text{H}_5)_2\text{C(CH}_3)\text{Cl}$, which is 3-chloro-3-methylpentane. Sodium in dry ether couples two of these to give the required product.
Options (A), (B) and (D) have the chlorine on C2 or C3 of a different skeleton and would couple to other alkanes.

Final Answer:
Option (C). \[ \boxed{\text{3-chloro-3-methylpentane (C)}} \]
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