Question

Identify the product/s formed in the following reaction 
 

 

• A. 1
• B. 2
• C. 3
• D. 4

Hint:

Aryl alkyl ethers on heating with \(HBr\) or \(HI\) cleave at the alkyl-oxygen bond because the aryl-oxygen bond has partial double bond character due to resonance.

Answer 1

The Correct Option is A

Step 1: Identify the ether.
The given compound is an aryl alkyl ether.
It contains a phenyl group attached through oxygen to an isopropyl group: \[ C_6H_5-O-CH(CH_3)_2 \]

Step 2: Understand cleavage of aryl alkyl ether by \(HBr\).
When an aryl alkyl ether is heated with \(HBr\), cleavage occurs at the alkyl-oxygen bond.
The aryl-oxygen bond is not easily broken because it has partial double bond character due to resonance.
Therefore, \[ C_6H_5-O \] remains as phenol.

Step 3: Formation of products.
The isopropyl group forms isopropyl bromide: \[ (CH_3)_2CHBr \] The phenoxy part forms phenol: \[ C_6H_5OH \] Thus, the reaction is: \[ C_6H_5-O-CH(CH_3)_2+HBr \rightarrow C_6H_5OH+(CH_3)_2CHBr \]

Step 4: Final conclusion.
Hence, the products formed are \[ \boxed{\text{Phenol and 2-bromopropane}} \]