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JEE Advanced levelNumerical answerDifficulty 3 of 3g3261

Count the distinct enolate anions (removal of one alpha proton, drawn as enolate ) that can be derived from the ketone shown, counting E and Z geometrical isomers of an enolate separately. Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 3

The ketone shown is 2-methylpentan-3-one. Deprotonation of the tertiary CH gives one enolate, , which has two identical methyl groups on one carbon and so no E/Z isomerism. Deprotonation of the CH gives , which exists as E and Z isomers. The total is , confirmed by RDKit enumeration.
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