Dolbier HW Solutions 530

Dolbier HW Solutions 530 - 624 AMINES (e) The target amino...

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( e ) The target amino alcohol is the product of nucleophilic ring opening of 1,2-epoxypropane by ammonia. Ammonia attacks the less hindered carbon of the epoxide function. The necessary epoxide is formed by epoxidation of propene. ( f ) The reaction sequence is the same as in part ( e ) except that dimethylamine is used as the nucleo- phile instead of ammonia. ( g ) The key to performing this synthesis is recognition of the starting material as an acetal of acetophenone. Acetals may be hydrolyzed to carbonyl compounds. Once acetophenone has been obtained, it may be converted to the required product by reduc- tive amination. 22.30 ( a ) The reaction of alkyl halides with N -potassiophthalimide (the f rst step in the Gabriel synthe- sis of amines) is a nucleophilic substitution reaction. Alkyl bromides are more reactive than
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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