Chapter 22: Q12P (page 1161)
Propose a mechanism for the reaction of cyclohexyl methyl ketone with excess bromine in the presence of sodium hydroxide.
Short Answer

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Chapter 22: Q12P (page 1161)
Propose a mechanism for the reaction of cyclohexyl methyl ketone with excess bromine in the presence of sodium hydroxide.

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The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.

Predict the major products of the following reactions.
a)

Propose mechanisms for the following reactions.

Without looking back, propose a mechanism for the hydrolysis of this iminium salt to the alkylated ketone. The first step is attack by water, followed by loss of a proton to give a carbinolamine. Protonation on nitrogen allows pyrrolidine to leave, giving the protonated ketone.
Question:Show how you would use an aldol, Claisen, or another type of condensation to make each compound
f.

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