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Acid Catalysed Acetal Formation

Question

Which of the following reagents would distinguish cis-cyclopenta $- 1, 2 - d i o l$ from the trans-isomer?
$O z o n e$
$A c e t o n e$
$M n O_{2}$
$A l u m i n i u m i s o p r o p o x i d e$

A

O z o n e

B

A l u m i n i u m i s o p r o p o x i d e

C

A c e t o n e

D

M n O_{2}

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Solution

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Acetone would distinguish cis-cyclopenta−1,2−diol from the trans-isomer.
With cis isomer, acetone forms bicylic ketal. With trans isomer, formation of bicyclic ketal is not possible due to presence of angle strain.

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