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Unformatted text preview: Practice Problem 5‐13 – Answer Show the product of Claisen condensation of each ester. (a) Ethyl phenylacetate in the presence of sodium ethoxide (b) Methyl hexanoate in the presence of sodium methoxide Practice Problem 5‐14 – Answer When a 1:1 mixture of ethyl propanoate and ethyl butanoate is treated with sodium ethoxide, four Claisen condensation products are possible. Draw a structural formula for each product. Practice Problem 5‐15 – Answer Draw structural formulas for the β‐ketoesters formed by Claisen condensation of ethyl propanoate with each ester. Practice Problem 5‐16 – Answer Draw a structural formula for the product of saponification, acidification, and decarboxylation of each β‐ketoester formed in Practice Problem 5‐15. (a) (b) (c) Practice Problem 5‐17 – Answer The Claisen condensation can be used as one step in the synthesis of ketones, as illustrated by this reaction sequence. Propose structural formulas for compounds A and B and the ketone formed in this sequence. Practice Problem 5‐18 – Answer Propose a synthesis for each ketone, using as one step in the sequence a Claisen condensation and the reaction sequence illustrated in Practice Problem 5‐17. Practice Problem 5‐19 – Answer Propose a mechanism for the following conversion. Practice Problem 5‐20 – Answer Claisen condensation between diethyl phthalate and ethyl acetate followed by saponification, acidification, and decarboxylation forms a diketone, C9H6O2. Propose structures for compounds A, B, and the diketone. Practice Problem 5‐21 – Answer Propose a sequence of reactions to prepare the indicated target compound from the indicated starting material. You may also use any other organic and/or inorganic reagents necessary. ...
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- Summer '08