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Question

Which of the following pairs cannot be differentiated by Tollens' reagent?

A
Benzaldehyde and benzyl alcohol
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B
Hexanal and 2-hexanone
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C
2-Hexanol and 2-hexanone
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D
Pentanal and diethyl ether
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Solution

The correct option is C 2-Hexanol and 2-hexanone
Tollen's reagent give positive test with aliphatic aldehydes, aromatic aldehydes and α-hydroxy ketone.

Tollen's is used to differentiate aldehyde and ketone.

In (a), benzaldehyde gives positive test for tollen's reagent hence, this pair can be differentiated.

In (b), hexanal gives positive test for tollen's reagent hence, this pair can be differentiated.

In (c), both 2-hexanol and 2-hexanone gives negative test for tollen's reagent so they cannot be differentiated.

In (d), pentanal gives positive test for tollen's reagent hence, this pair can be differentiated.

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