Chemistry - GOC Question with Solution | TestHub

ChemistryGOCRESONANCE AND MESOMERIC EFFECTMedium2 minQB
ChemistryMediumsingle choice

Arrange the following in decreasing order of % enol content.

(I) structure (II) structure (III) structure

Options:

Answer:
C
Solution:

Enol content depends on how much the enol form is stabilised.

(III) Pentane-2,4-dione is a 1,3-diketone: its enol is conjugated and strongly hydrogen bonded (about 80% enol).

(II) Ethyl acetoacetate is a β-ketoester: the same stabilisation, but the ester is a weaker acceptor because of its own resonance (about 8% enol).

(I) Propanone has no such stabilisation (about % enol).

Order: III II I.

Answer: (C).

Stream:JEESubject:ChemistryTopic:GOCSubtopic:RESONANCE AND MESOMERIC EFFECT
⏱ 2mℹ️ Source: QB

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