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General Chemistry Principles, Patterns, and Applications, 2011

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Solution:<br />

a. The proton on the carboxylic acid functional group is acidic. Thus reacting a<br />

carboxylic acid with a strong base is an acid–base reaction, whose products are a salt—in<br />

this case, C 6H 5CH 2CO<br />

−<br />

2 —<strong>and</strong> water.<br />

K+<br />

b. The nitrogen of cyclohexylamine contains a lone pair of electrons, making it an excellent<br />

nucleophile, whereas the carbonyl carbon of ethyl acetate is a good electrophile. We<br />

therefore expect a reaction in which nucleophilic attack on the carbonyl carbon of the<br />

ester produces an amide <strong>and</strong> ethanol. The initial site of attack <strong>and</strong> the reaction products<br />

are as follows:<br />

Exercise<br />

Predict the products of each reaction. State the initial site of attack.<br />

a. acetic acid with 1-propanol<br />

b. aniline (C 6H 5NH 2) with propyl acetate [CH 3C(=O)OCH 2CH 2CH 3]<br />

Answer:<br />

a. Initial attack occurs with protonation of the oxygen of the carbonyl. The products are:<br />

Saylor URL: http://www.saylor.org/books<br />

Saylor.org<br />

2298

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