14_Amines - Chem 267 Basic Organic Chemistry II Prof. Dr....

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Prof. Dr. Xiangdong Fang University of Waterloo Chem 267 Basic Organic Chemistry II 1
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2 Amine Nomenclature Notes: (1) Simple amines are named after the corresponding alkanes; (2) If more than one types of alkyl groups are attached to N, the largest alkyl group is considered as the parent, and the subsidiary alkyl group is designated by an N-alkyl prefix; (3) If two or three amino groups are the same, the prefixes di- or tri- are used; (4) If two amino groups are present, the compound is named as diamine;
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3 Geometric Isomers of Amine Molecules “amines with three different groups are chiral, but the enantiomers cannot be Isolated, because of the rapid interconvertion via a planar transition state” Note: Some 4 o ammonium salts can be isolated as pure enantiomers
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4 Synthesis of Amines A ) Reactions with alkyl halides: S N 2 mechanism Note: The reaction is not suitable for preparation of amines, because in the absence of large amount of NH 3 , a mixture of 1 o , 2 o , 3 o amines and 4 o ammonium salts are formed.
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5 B ) Azide Reduction to make 1 o amines C ) Gabriel Amine Synthesis to make 1 o amines
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6 Mechanism of Gabriel Synthesis
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14_Amines - Chem 267 Basic Organic Chemistry II Prof. Dr....

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