Enolates act as nucleophiles through carbon, attacking a large number of electrophiles (haloalkanes, epoxides, carbonyls, esters...). At this point we will focus on the reaction between enlolates and haloalkanes, which allows the addition of carbon chains to the a position of the chain.

Cyclohexanone is converted to 2-Methylcyclohexanone by treatment with LDA followed by methyl iodide.

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Stages of the mechanism by which cyclohexanone is alkylated:

Stage 1. Formation of the enolate
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Stage 2. Nucleophilic attack of the enolate on the haloalkane (SN2 type reaction)
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Alkylation reactions have two major problems.
1. Competition with aldol condensation. Carbonyls in a basic medium tend to condense to form aldols.
2. The reaction is difficult to control and tends to polyalkylate the carbonyl.

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