2. The hydrolysis of a nitrile under acidic or basic conditions to form a carboxylic acid parent functional group is a difficult reaction to perform in the laboratory. This is due to a few factors including the necessity of two or more equivalents of the reagent (H,O" or "OH) and excessive heat during the entire reaction. Because of this, in the laboratory, the nitrile is usually hydrolyzed to a primary amide under mild conditions (20 °C) (scheme (1). Then, in a separate reaction, the primary amide is hydrolyzed to a carboxylic acid under harsh conditions (100 °C) (scheme (2). H,SO, `NH2 (1) 20 °C H,SO, `NH2 OH (2) H,0 100 °C a. Explain why the reaction in scheme (1) is easily done under mild conditions and the reaction in scheme (2) needs much more harsh conditions in complete sentences. b. Draw the complete mechanism of the reaction for scheme (1).

2. The hydrolysis of a nitrile under acidic or basic conditions to form a carboxylic acid parent functional group is a difficult reaction to perform in the laboratory. This is due to a few factors including the necessity of two or more equivalents of the reagent (H,O" or "OH) and excessive heat during the entire reaction. Because of this, in the laboratory, the nitrile is usually hydrolyzed to a primary amide under mild conditions (20 °C) (scheme (1). Then, in a separate reaction, the primary amide is hydrolyzed to a carboxylic acid under harsh conditions (100 °C) (scheme (2). H,SO, `NH2 (1) 20 °C H,SO, `NH2 OH (2) H,0 100 °C a. Explain why the reaction in scheme (1) is easily done under mild conditions and the reaction in scheme (2) needs much more harsh conditions in complete sentences. b. Draw the complete mechanism of the reaction for scheme (1).

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter20: Acidity And Pka Of Phenols

Section: Chapter Questions

Problem 11E

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