Question:hard

An organic compound \(C_4H_9Br\) (A) on reaction with Na/dry ether gave B. Photochemical chlorination of B gave two monochlorides. Correct statement regarding A is:

Show Hint

Primary alkyl halides generally prefer \(S_N2\) substitution with alkoxide ions, whereas tertiary alkyl halides favor elimination and \(S_N1\) pathways.
Updated On: Jun 17, 2026
  • It is a chiral molecule
  • It undergoes nucleophilic substitution by \(S_N1\) mechanism
  • Reaction of it with \(NaOC_2H_5\) gave predominantly substitution product
  • It can be obtained by the addition of HBr to but-2-ene
Show Solution

The Correct Option is C

Solution and Explanation

Step 1: Read the clues about A.
The compound A is $C_4H_9Br$. It reacts with sodium in dry ether (a Wurtz reaction) to give B. Then light-driven chlorination of B gives only two monochlorides. These clues fix what A is.
Step 2: Identify B from the Wurtz reaction.
The Wurtz reaction joins two alkyl halides into a bigger alkane. The bromide that gives an alkane producing just two monochlorides is the straight-chain $n$-butyl bromide. So B is $n$-octane.
Step 3: Confirm A is a primary bromide.
Since B comes from a straight-chain bromide, A is $n$-butyl bromide, a primary alkyl halide ($CH_3CH_2CH_2CH_2Br$).
Step 4: Test the reaction with sodium ethoxide.
Primary alkyl halides favour substitution over elimination with a nucleophile. With sodium ethoxide, \[ RBr + NaOC_2H_5 \rightarrow ROC_2H_5 + NaBr, \] so substitution mainly happens. This matches the correct option.
Step 5: Reject the other statements.
A primary bromide has no four different groups on one carbon, so it is not chiral. Primary halides do not go by $S_N1$ (they prefer $S_N2$). Adding HBr to but-2-ene gives 2-bromobutane, not $n$-butyl bromide.
Step 6: State the correct statement.
So the right statement about A is \[ \boxed{\text{reaction with } NaOC_2H_5 \text{ gives mainly substitution}} \]
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