JEE Main · 2024 · 04 Apr 2024 · Shift 1 · General Organic Chemistry

Identify (B) and (C) and how are (A) and (C) related?

1. (A)(see structure) (see structure) functional group isomers

   

   

2. (B)(see structure) (see structure) Derivative

   

   

3. (C)(see structure) (see structure) position isomers

   

   

   ✓ Correct
4. (D)(see structure) (see structure) chain isomers

   

   

Answer: (C)

Solution

$A\stackrel{\text{alc. NaOH (E2)}}{\to }B(\text{alkene})\stackrel{\text{HBr/ether}}{\to }C.$
Elimination moves the halogen off, forming the double bond; HBr then adds back (Markovnikov) to give $C$, in which the bromine sits at a different carbon than in $A$. Thus $A$ and $C$ have the same skeleton and functional group but the substituent in a different position — they are position isomers. Option C.

JEE Main · 2024 · 04 Apr 2024 · Shift 1 · Single correct option