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Chapter 23: Carbonyl Condensation Reactions

Q22P

Page 777

How would you prepare the following compound using a Robinson annulation reaction between a饾泝-diketone and an饾泜,饾泝 -unsaturated ketone? Draw the structures of both reactants and the intermediate Michael addition product

Q23-10P

Page 764

Q23-11P

Page 766

Show the products you would expect to obtain by Claisen condensation of the following esters:(a) (CH3)2CHCH2CO2Et (b) Ethyl phenylacetate (c) Ethyl cyclohexyl acetate

Q23-12P

Page 766

As shown in Figures 23-4, the Claisen reaction is reversible. That is, a饾泝-keto ester can be cleaved by base into two fragments. Using curved arrows to indicate electron flow, show the mechanism by which this cleavage occurs.

Q23-13P

Page 768

What product would you expect from the following mixed Claisen-like reaction?

Q23-15P

Page 770

Dieckmann cyclization of diethyl 3-methylheptanedioate gives a mixture of two饾泝-keto ester products. What are their structures, and why is a mixture formed?

Q23-20P

Page 775

Show how you might use an enamine reaction to prepare each of the following compounds:

Q23-3P

Page 759

What enone product would you expect from aldol condensation of each of the following compounds?

Q23-4P

Page 759

Aldol condensation of 3-methyl cyclohexanone leads to a mixture of two enone products, not counting double-bond isomers. Draw them.

Q23-5P

Page 760

Which of the following compounds are aldol condensation products? What is the aldehyde or ketone precursor of each?

(a) 2-Hydroxy-2-methylpentanal (b) 5-Ethyl-4-methyl-4-hepten-3-one

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