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Question:

Which of the following reagents would distinguish cis-cyclopenta-1,2-diol from the trans-isomer?

Ozone

Aluminium isopropoxide

Acetone

MnO2

Solution:

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