Dolbier HW Solutions 528 - CH 3 CH 2 CH 2 CH 2 CH 2 NH 2 1...

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Diethylamine can also be prepared by reductive amination of acetaldehyde [from part ( a )] with ethylamine. ( d ) The preparation of N , N -diethylacetamide is a standard acylation reaction. The reactants, acetyl chloride and diethylamine, have been prepared in previous parts of this problem. ( e ) Triethylamine arises by reduction of N , N -diethylacetamide or by reductive amination. ( f ) Quaternary ammonium halides are formed by reaction of alkyl halides and tertiary amines. 22.29 ( a ) In this problem a primary alkanamine must be prepared with a carbon chain extended by one carbon. This can be accomplished by way of a nitrile. The desired reaction sequence is therefore 1-Butanol CH 3 CH 2 CH 2 CH 2 OH Butyl bromide CH 3 CH 2 CH 2 CH 2 Br Pentanenitrile CH 3 CH 2 CH 2 CH
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Unformatted text preview: CH 3 CH 2 CH 2 CH 2 CH 2 NH 2 1. LiAlH 4 2. H 2 O PBr 3 or HBr NaCN RCH 2 NH 2 RCN RBr ROH (R ) 5 CH 3 CH 2 CH 2 CH 2 Triethylamine (CH 3 CH 2 ) 3 N 1 Ethyl bromide CH 3 CH 2 Br Tetraethylammonium bromide (CH 3 CH 2 ) 4 N Br 2 1 Diethylamine (CH 3 CH 2 ) 2 NH 1 Acetaldehyde CH 3 CH O Triethylamine (CH 3 CH 2 ) 3 N H 2 , Ni or NaBH 3 CN N , N-Diethylacetamide O CH 3 CN(CH 2 CH 3 ) 2 Triethylamine (CH 3 CH 2 ) 3 N 1. LiAlH 4 2. H 2 O Diethylamine (CH 3 CH 2 ) 2 NH 1 Acetyl chloride CH 3 CCl O N , N-Diethylacetamide O CH 3 CN(CH 2 CH 3 ) 2 HO 2 Ethylamine CH 3 CH 2 NH 2 1 Acetaldehyde CH 3 CH O Diethylamine CH 3 CH 2 NHCH 2 CH 3 H 2 , Ni or NaBH 3 CN 622 AMINES...
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