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Question

In the reaction 

the major product [X] is

The correct answer is
racemic trans-1,2-cyclohexanediol diacetate

The given reaction involves the conversion of an optically pure trans-2-acetoxycyclohexyl tosylate to a product, let's determine what the major product [X] will be:

  1. The reaction uses acetic acid (HOAc) and potassium acetate (KOAc) under heating (\Delta), which is a classic setup for an esterification or functional group transformation.
  2. Since the starting material is optically pure and trans, the inversion of configuration can be expected in the mechanism, typically through an SN2 reaction mechanism.
  3. During SN2 reaction, nucleophilic substitution will result in the inversion of the configuration at the carbon where the leaving group (tosylate) was attached.
  4. However, since the product [X] is already in the trans configuration, the SN2 reaction doesn't alter the relative stereochemistry of the two substituents on the cyclohexane ring.
  5. Thus, the product will be racemic because the reaction produces a mixture of enantiomers resulting in no net optical activity due to their racemic nature.
  6. Consequently, the major product [X] is racemic trans-1,2-cyclohexanediol diacetate.
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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. 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 

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