Major products (C) and (D) will be respective | vedclass

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

Question

(A) The starting material is $trans-2-methylcyclohexanol$. $1$. Reaction with $SOCl_2$ (without pyridine) proceeds via an $S_Ni$ mechanism,which invol

Vedclass · Accepted Answer

$3-$methylcyclohexene and $1-$methylcyclohexene

Vedclass · Answer

(A) The starting material is $trans-2-methylcyclohexanol$. $1$. Reaction with $SOCl_2$ (without pyridine) proceeds via an $S_Ni$ mechanism,which involves retention of configuration. Thus,$(A)$ is $trans-1-chloro-2-methylcyclohexane$. Subsequent elimination with $alc. KOH$ follows an $E2$ mechanism. For $E2$ elimination,the leaving group $(Cl)$ and the $\beta-H$ must be anti-periplanar. In $trans-1-chloro-2-methylcyclohexane$,the $\beta-H$ at $C-1$ is anti to the $Cl$ atom,leading to the formation of $3-methylcyclohexene$ as the major product $(C)$. $2$. Reaction with $SOCl_2$ in the presence of pyridine proceeds via an $S_N2$ mechanism,which involves inversion of configuration. Thus,$(B)$ is $cis-1-chloro-2-methylcyclohexane$. Subsequent elimination with $alc. KOH$ follows an $E2$ mechanism. In $cis-1-chloro-2-methylcyclohexane$,the $\beta-H$ at $C-2$ is anti to the $Cl$ atom,leading to the formation of the more stable,more substituted alkene,$1-methylcyclohexene$,as the major product $(D)$.

Major products $(C)$ and $(D)$ will be respectively:

Similar Questions

Which combination of alkyl bromide and epoxide can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the epoxide?

$CHO-CH(OH)-CH_2OH \xrightarrow{2HIO_4}$ Products obtained in the above reaction are

Which of the following can be used to test the acidic nature of ethanol?

The number of primary isomeric alcohols with the molecular formula $C_4H_{10}O$ is:

What is glycerol?

Vedclass Test Series

Exam Paper Generator

Online Exam Module