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Chapter 22: Carbonyl Alpha-Substitution Reactions

Q44E

Page 752

Which, if any, of the following compounds can be prepared by an acetoacetic ester synthesis? Explain.

Q4P

Page 734

Write the complete mechanism for the deuteration of acetone on treatment with D3O+.

Q6P

Page 735

If methanol rather than water is added at the end of a Hell鈥揤olhard鈥揨elinskii reaction, an ester rather than an acid is produced. Show how you would carry out the following transformation, and propose a mechanism for the ester forming step.

Q8P

Page 738

Draw a resonance structure of the acetonitrileanion,

andaccount for the acidity of nitriles.

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