Optically active (S)-2-methoxypropanal on rea | vedclass

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

Question

(B) The starting material is $(S)-2-$methoxypropanal. Reaction with $MeMgX$ (Grignard reagent) follows the Felkin-Anh model to produce a mixture of di

Vedclass · Accepted Answer

$II$

Vedclass · Answer

(B) The starting material is $(S)-2-$methoxypropanal. Reaction with $MeMgX$ (Grignard reagent) follows the Felkin-Anh model to produce a mixture of diastereomeric alcohols.The major product $P$ is the one where the bulky groups are arranged to minimize steric hindrance.Upon treatment with $MeI / K_2CO_3$,the hydroxyl group $(-OH)$ is methylated to form an ether $(-OCH_3)$.For the final product to be optically inactive,it must be a meso compound (possessing a plane of symmetry).Structure $II$ represents the $(2S, 3S)$ or $(2S, 3R)$ configuration depending on the attack. The meso compound formed after methylation is the $(2S, 3R)-2,3-$dimethoxybutane,which has a plane of symmetry.Thus,$P$ corresponds to structure $II$.

Optically active $(S)-2-$methoxypropanal on reaction with $MeMgX$ gives a mixture of alcohols. The major diastereomer $P$ on treatment with $MeI / K_2CO_3$ gives an optically inactive compound. $P$ is

Similar Questions

The structural formula of sativene is shown below. How many stereogenic centers are there in this molecule?

Which of the following properties is $NOT$ identical for enantiomers?

The property by virtue of which a compound can rotate the plane of plane-polarized light is known as:

The number of possible stereoisomers for a compound containing three different chiral centers is .............

Which among the following compounds has a chiral carbon atom?

Vedclass Test Series

Exam Paper Generator

Online Exam Module