Q59E
Question
The two isomers cis- and trans-4-tert-butyl-2-methylcyclohexanone are interconverted by base treatment. Which isomer do you think is more stable, and why?
Step-by-Step Solution
Verified Answer
Cis-4-tert-butyl-2-methylcyclohexanone is more stable.
1Step 1: Isomers cis - and trans -4- tert -butyl-2-methylcyclohexanone
The reaction of cis—4-terbutyl-2-methylcyclohexanone with NaOH undergoes isomerisation.
Isomerisation
2Step 2: Stability of isomer
The cis-isomer is more stable. This is because both substituted groups are at the equatorial position of the cyclohexane ring and cause less 1,3diaxial interaction.
The chair forms of both the isomers are as shown below:
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