All Exams Test series for 1 year @ ₹349 only
Question

Hydration of fumaric acid gives malic acid as shown below. Assume that addition of water takes place specifically from A face or B face. The correct statement pertaining to stereochemistry of malic acid formed is 

The correct answer is
addition specifically from A face gives S isomer of malic acid

To determine the stereochemistry of the malic acid formed by the hydration of fumaric acid, we must consider the mechanism of addition and the configuration it results in.

Fumaric acid is a trans isomer, and during the hydration, water adds to the double bond. The addition of water can occur from either the "A face" or the "B face" of the double bond.

  1. Concept of Stereochemistry:
    • The addition of groups to a double bond can create chiral centers, resulting in stereoisomers.
    • In this case, the center becomes chiral after the addition of water, and the configuration (R or S) depends on the direction of the addition.
  2. Addition from the A Face:
    • When water adds from the "A face," the orientation of the groups is such that the order of substituents around the chiral center aligns with the S configuration.
  3. Other Options:
    • Adding from the "B face" doesn't result in the S isomer; it would actually give a different stereochemical outcome.
    • The statement about a racemic mixture isn't correct in the case of specific face addition because each face leads to a specific stereoisomer.

Conclusion: The correct statement is that addition specifically from the A face gives the S isomer of malic acid.

Was this answer helpful?

Important Questions from Stereochemistry

  1. The specific rotation of enantiomerically pure (S)-2-butanol is $+14^\circ$. The specific rotation of enantiomeric mixture of 2-butanol obtained from an asymmetric reduction of 2-butanone is found to be $+7^\circ$. The percentage of (R)-2-butanol present in the reaction mixture is ________ (in integer).

  2. In the following reaction, 13.4 grams of aldehyde P gave a diastereomeric mixture of alcohols Q and R in a ratio of 2:1. If the yield of the reaction is 80%, then the amount of Q (in grams) obtained is ________ (in integer).

  3. The correct statement(s) about the relationship for the H-atoms in the following compounds is (are):

  4. The number of possible stereoisomers for cyclononene is ______________

  5. The number of possible stereoisomers obtained in the following reaction is _____________

Need Expert Advice?

Start Your Preparation with Prepp Mobile App

Download the app from Google Play & App Store
Download the app from Google Play & App Store
Prepp Mobile App