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Question
A stereoisomer of cyclobutane-1,2-diol has lower solubility in water than its other stereoisomer. Which is this isomer and why?
A stereoisomer of cyclobutane-1,2-diol has lower solubility in water than its other stereoisomer. Which is this isomer and why?
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Solution
The correct option is A Cis, intramolecular H-bonding
Cis isomer of acyclic system is less stable than trans isomer. This is due to the steric hindrance between the terminal groups is always greater in Cis isomer than trans isomer.
When there is H-bonding arise in cis isomer, cis become more stable than trans form.
here due to intramolecular hydrogen bonding, cis-cyclobutane-1,2-diol is more stable than trans form. Hence, the correct answer is option (a).
Cis isomer of acyclic system is less stable than trans isomer. This is due to the steric hindrance between the terminal groups is always greater in Cis isomer than trans isomer.
When there is H-bonding arise in cis isomer, cis become more stable than trans form.
here due to intramolecular hydrogen bonding, cis-cyclobutane-1,2-diol is more stable than trans form. Hence, the correct answer is option (a).
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