Dolbier HW Solutions 527

Dolbier HW Solutions 527 - 2CH 3 CH 2 NH 2 1 Acetyl...

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Two of these methods, the Gabriel synthesis and the preparation and reduction of the corresponding azide, begin with ethyl bromide. To use reductive amination, we must begin with oxidation of ethanol to acetaldehyde. Another possibility is reduction of acetamide. This requires an initial oxidation of ethanol to acetic acid. ( b ) Acylation of ethylamine with acetyl chloride, prepared in part ( a ), gives the desired amide. Excess ethylamine can be allowed to react with the hydrogen chloride formed in the acylation reaction. Alternatively, equimolar amounts of acyl chloride and amine can be used in the pres- ence of aqueous hydroxide as the base. ( c ) Reduction of the N -ethylacetamide prepared in part ( b ) yields diethylamine. N -Ethylacetamide CH 3 CNHCH 2 CH 3 O Diethylamine CH 3 CH 2 NHCH 2 CH 3 1. LiAlH 4 2. H 2 O Ethylamine
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Unformatted text preview: 2CH 3 CH 2 NH 2 1 Acetyl chloride CH 3 CCl O 1 N-Ethylacetamide CH 3 CNHCH 2 CH 3 O Ethylammonium chloride CH 3 CH 2 NH 3 Cl 2 1 Acetic acid CH 3 CO 2 H Ethylamine CH 3 CH 2 NH 2 K 2 Cr 2 O 7 , H 2 SO 4 H 2 O, heat Ethanol CH 3 CH 2 OH Acetamide CH 3 CNH 2 O 1. SOCl 2 2. NH 3 1. LiAlH 4 2. H 2 O Ethylamine CH 3 CH 2 NH 2 NH 3 , H 2 , Ni Acetaldehyde CH 3 CH O Ethanol CH 3 CH 2 OH PCC or PDC CH 2 Cl 2 Acetaldehyde CH 3 CH O Ethyl azide CH 3 CH 2 N 3 Ethylamine CH 3 CH 2 NH 2 Ethyl bromide CH 3 CH 2 Br NaN 3 1. LiAlH 4 2. H 2 O 1 N 2 K 1 O O N-Potassiophthalimide NCH 2 CH 3 O O N-Ethylphthalimide CH 3 CH 2 NH 2 Ethylamine CH 3 CH 2 Br Ethyl bromide H 2 NNH 2 Ethanol CH 3 CH 2 OH Ethyl bromide CH 3 CH 2 Br PBr 3 or HBr AMINES 621...
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