Arrange the following in decreasing order of enol content.
i. Diethyl malonate
ii. Acetoacetic ester(AAE or EAA)
iii. Acetyl acetone
iv. PhCOCH $_{2}$ COCH $_{3}$

(iv) > (iii) > (ii) > (i)

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(iv) > (iii) > (i) > (ii)

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(iii) > (iv) > (ii) > (i)

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(iii) > (iv) > (i) > (ii)

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Solution

The correct option is A (iv) > (iii) > (ii) > (i)
The decreasing order of enol content is $(i v) > (i i i) > (i i) > (i)$ or $P h C O C H_{2} C O C H_{3} >$ acetyl acetone > acetoacetic ester > diethyl malonate.
(a) Ketonic form predominates in simple monocarbonyl compounds.
(b) Enolic form predominates in compounds containing two carbonyl compounds separated by a methylene group, i.e, 1,3-dicarbonyl compounds.
(c) Intramolecular hydrogen bonds between enolic hydroxyl group and second carboxyl group increases the enol content.

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