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Unformatted text preview: 4. Draw a mechanism for the following reactions. 5. (a) Enamines are excellent precursors to monoalkylated ketones. Provide a mechanism for the following reactions: (b) An advantage of enamines is that they provide monoalkylated ketones in fairly good yields. In fact, direct monoalkylation of cyclohexanone (i.e. adding methyl iodide directly to the enolate of cyclohexanone) does not work very well. Why is that? (c) It has been suggested that the real advantage to the use of enamines is that they contain a nucleophilic carbon. Identify this carbon in the enamine shown above. What is the ultimate source of electrons that it uses in acting as a nucleophile? (d) What product (X) would result in (a) above if benzoyl chloride was used instead of methyl chloride? Now, suppose that X is further treated with (i) sodium ethoxide and (ii) methyl iodide. What product (Z) would result?...
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