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Draw the product obtained when each of the following

Chapter 22, Problem 22.71

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QUESTION:

Draw the product obtained when each of the following compounds is heated in the presence of a base to give an aldol condensation: O (a) H O (b) H O (c)

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QUESTION:

Draw the product obtained when each of the following compounds is heated in the presence of a base to give an aldol condensation: O (a) H O (b) H O (c)

ANSWER:

Step 1 of 4

Recall that the protons located on a carbon adjacent to carbonyl (“alpha protons”) are unusually acidic, as the resulting conjugation base is resonance-stabilized. This conjugate base (known as an enolate) can act as a nucleophile and attack another molecule of starting material at the electrophilic carbonyl carbon. This resulting alcohol can then be dehydrated under the hot, basic reaction conditions. This is a general description of an aldol condensation reaction.

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