- A

- B

- C

- D

View written solutionFree
Correct answer: C
- Find the molecular formula
Given percentage composition:
Take compound:
- C mol
- H mol
- Br mol
Divide by the smallest:
- C:
- H:
- Br:
So the formula is approximately .
Check molar mass: Using bromine as : Hence molecular formula is:
- Use oxidation products
Both isomers on oxidation with give:
- (A) benzoic acid
- (B) -bromobenzoic acid
Oxidation of alkyl side chains on benzene converts the entire side chain to , provided there is at least one benzylic H.
- If oxidation gives benzoic acid, then bromine is in the side chain, not on the ring.
- If oxidation gives -bromobenzoic acid, then bromine is on the ring and the oxidizable alkyl group is para to it.
So:
- (A) must be a brominated side-chain derivative of ethylbenzene type.
- (B) must be a bromine-substituted ring compound with an ethyl group para to Br.
- Identify isomer A
Formula:
A gives benzoic acid on oxidation, so likely structure is: This is 1-bromo-1-phenylethane.
Check properties:
- It has a chiral carbon attached to:
Hence it is optically active.
- With alcoholic , benzylic bromides react readily and give , a pale yellow precipitate.
So (A) is:
- Identify isomer B
B gives -bromobenzoic acid on oxidation, so bromine must be on the benzene ring and the side chain must oxidize to .
With formula , the suitable structure is: This is -bromoethylbenzene.
On oxidation: which is -bromobenzoic acid.
- Final identification
Thus,
So the correct option is the one containing:
- Comparison with stored answer
Stored correct answer: C
Our derived answer is also C.
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