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Question

Question: CH3 OH ...

CH3

OH

A

Racemic

B

Diastereomers

C

G.I

D

Positional isomers

Answer

Diastereomers

Explanation

Solution

  1. We have a cyclohexanol derivative with two stereogenic centers: one carbon bearing a CH₃ group and an adjacent carbon bearing an OH group. In the starting compound both substituents are shown as wedge (coming out of the plane) so the configuration is fixed (say, 1R,2R).

  2. Under acidic and heated conditions (H⁺, Δ), the –OH group is protonated and leaves as water forming a planar carbocation at C₂.

  3. Nucleophilic attack by water on this carbocation can occur from either face. Thus, the configuration at C₂ is scrambled.

  4. Since the configuration at C₁ (with CH₃) remains unchanged, the two products formed will be 1R,2R and 1R,2S.

  5. These two products are not mirror images (they differ only at one stereocenter) and hence are diastereomers.