Consider the following reaction sequence:Cycl | vedclass

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

Question

(A, D) The reaction of $methylenecyclohexane$ with $Br_2$ in $CH_3OH$ is a halohydrin-type reaction (specifically,a haloetherification).$1$. The $Br_2

Vedclass · Accepted Answer

Vedclass · Answer

(A, D) The reaction of $methylenecyclohexane$ with $Br_2$ in $CH_3OH$ is a halohydrin-type reaction (specifically,a haloetherification).$1$. The $Br_2$ forms a cyclic bromonium ion with the double bond of $methylenecyclohexane$.$2$. The nucleophile $CH_3OH$ attacks the more substituted carbon (the one attached to the cyclohexane ring) to open the bromonium ring,following Markovnikov-like regioselectivity due to the stability of the developing carbocation character.$3$. This yields $A$,which is $1-(bromomethyl)-1-methoxycyclohexane$.$4$. In the next step,$A$ reacts with $KCN$. The $CN^-$ ion acts as a nucleophile and performs a nucleophilic substitution $(S_N2)$ on the primary alkyl bromide ($CH_2Br$ group).$5$. The $Br$ atom is replaced by the $CN$ group,resulting in $B$,which is $1-(cyanomethyl)-1-methoxycyclohexane$.

Similar Questions

Nitrochloroform (Chloropicrin) is prepared by the action of chloroform and:

The major product obtained when this substrate is subjected to $E_2$ reaction under the treatment of potassium $tert$-butoxide is:

Which of the following gases is formed during the oxidation of trichloromethane?

The reactivity of alkyl bromides towards iodide ion in dry acetone decreases in the order:
$I. CH_3CH_2Br$
$II. CH_3-CH(CH_3)-Br$
$III. CH_3-C(CH_3)_2-Br$
$IV. CH_3Br$

The following compound on hydrolysis in aqueous acetone will give:

Vedclass Test Series

Exam Paper Generator

Online Exam Module