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  • Which of the following compounds will show the maximum 'enol' content? Option: 1

Which of the following compounds will show the maximum 'enol' content?
Option: 1 CH_{3}COCH_{2}COOC_{2}H_{5}
Option: 2 CH_{3}COCH_{2}COCH_{3}
Option: 3 CH_{3}COCH_{3}
Option: 4 CH_{3}COCH_{2}CONH_{2}
 

Answers (1)

best_answer

Difinition of Tautomerism -

Tautomers are isomers of a compound that differ only in the position of the protons and electrons. The carbon skeleton of the compound is unchanged. A reaction that involves simple proton transfer in an intramolecular fashion is called tautomerism.

The stability of enol depends on the factors

(1) Resonance

(2) Hydrogen-bonding

(3) Hyperconjugation

(4) Hydrogen which is removed from \alpha- carbon should be acidic in Nature for enol formation.

CH2 is present between 2- electron-withdrawing group,  It is having acid 'H'

                        

Over the resonance effect decreases because of cross conjugation. So the stability of the enol form decreases.

The two -dicarbonyl compounds have a higher enol content than the two mono carbonyl compounds because hydrogen bonding and conjugation stabilize their enols. The enol content in C (a mono aldehyde) is higher than D because of the reasons outlined above. 

Therefore, option (2) is correct.

Posted by

Ritika Jonwal

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