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NEET 2016 Chemistry question

ChemistryOrganic Chemistry - Some Basic Principles and TechniquesNEET 2016

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

Answer: (1)

Solution

In the cis-1,2-diol the two groups lie on the same face of the five-membered ring, so they can bridge the carbonyl carbon of acetone and form a cyclic ketal (an acetonide, a five-membered 1,3-dioxolane ring fused to the cyclopentane ring): cis-diol Missing superscript or subscript argument+ (\text{CH}_3)_2$C=O

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Question ID VK-091897