Ch_322b_16.08 - Chapter 16.8 lecture note

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Addition of Derivatives of Ammonia, H 2 N-G : Derivatives of ammonia, H 2 N-G, react with aldehydes and ketones under acid-catalyzed conditions to produce imines . C :O: = + H 2 N- G H + C :N G + H 2 O imine R R' R' R Many imines of liquid aldehydes and ketones are solids, which were used in identifying the aldehydes and ketones by melting point about 100 years ago. Today the carbonyl compounds are more rapidly analyzed by spectroscopic methods. Typical Reaction Conditions for Imine Formation The ammonia derivatives usually are stored as their hydrochloride salts to prevent air oxidation. When used, the salts are added to a solution with a base such as sodium acetate that buffers the solution and produces the free base . O cyclohexanone + C 6 H 5 NHNH 3 Cl - + phenyl hydrazine hydrochloride N- NHC 6 H 5 a phenylhydrazone derivative Na + - O 2 CCH 3
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A Mechanism for Imine Formation C=O : + H + reversible protonation C=O H + C-O H + more reactive C=O H + + H 2 N- G nucleophilic addition
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This note was uploaded on 10/20/2009 for the course CHEM 322BL at USC.

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Ch_322b_16.08 - Chapter 16.8 lecture note

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