In the reaction shown below,the products are:

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

Question

(D) The reaction of anisole $(C_6H_5OCH_3)$ with $HBr$ involves the protonation of the ether oxygen atom by the acid.This is followed by the nucleophi

Vedclass · Accepted Answer

Phenol and $CH_3Br$

Vedclass · Answer

(D) The reaction of anisole $(C_6H_5OCH_3)$ with $HBr$ involves the protonation of the ether oxygen atom by the acid.This is followed by the nucleophilic attack of the bromide ion $(Br^-)$ on the less sterically hindered alkyl group.Since the phenyl group is attached to the oxygen,the $C-O$ bond between the phenyl ring and oxygen has partial double bond character due to resonance,making it stronger and harder to break.Therefore,the $Br^-$ ion attacks the methyl group $(CH_3)$,resulting in the formation of phenol $(C_6H_5OH)$ and methyl bromide $(CH_3Br)$.

Similar Questions

$Tert$-butyl methyl ether on treatment with hydrogen iodide in cold gives

Explain the reaction of anisole with $HI$.

Identify the missing product in the following reaction: $C_6H_5ONa + CH_3CH_2Br \rightarrow (?)$

The following are possible syntheses of phenyl propyl ether. Which one would work?
$(i)$ $C_6H_5OH$ $\xrightarrow{KNH_2}$ $\xrightarrow{CH_3CH_2CH_2Br}$
(ii) $CH_3CH_2CH_2OH$ $\xrightarrow{NaOH}$ $\xrightarrow{C_6H_5Br}$
(iii) $CH_3CH_2CH_2OH$ $\xrightarrow{NaH}$ $\xrightarrow{C_6H_5Br}$

Which of the following reactions is correctly represented?

Vedclass Test Series

Exam Paper Generator

Online Exam Module