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Draw the resonance structures of the enolate ions produced by the deprotonation of the below-given compounds through a base.
a. cyclopentane-1,3-dione
b. methyl acetoacetate
Predict the product of the reaction given below.
Draw the significant resonance forms for the following ketone when the α-carbon atom of the ketone is deprotonated to produce an enolate ion.
(i) pentan-3-one
(ii) cyclohexanone
Draw the enolate(s) formed by the treatment of the following molecule with a base.
Give the major product of the following reaction.
Draw the structure of the enol tautomer of the compound given below.
Draw the structures of the enol tautomers of the following compound and identify the more stable one.
The following reaction shows an acid-catalyzed rearrangement of a β,γ-unsaturated carbonyl compound to a more stable α,β-unsaturated compound. Draw a mechanism for this rearrangement.
Explain why the enol tautomer of 2,4-heptanedione is more stable in hexane than in water.
The rate of reaction for the exchange of α-hydrogen of acetone remains the same for acid-catalyzed chlorination, bromination, or deuterium substitution. What does this tell us about the mechanism of these reactions?
2-bromo-2-methyl-1-phenylpropan-1-one is produced through the acid-catalyzed bromination of 2-methyl-1-phenylpropan-1-one. Provide a mechanism for this reaction.
Draw an appropriate mechanism to demonstrate the base-promoted chlorination of acetone in the example below.
The haloform reaction involves the conversion of methyl ketone to carboxylate ion and haloform. Why do only methyl ketones form haloforms?