Chapter 23-1

Chapter 23-1 - CHEM 262 Wei You Chapter 23 Amines(1 1...

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1 CHEM 262 Wei You Chapter 23. Amines (1)
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Structure and Classification 1°, 2°, or , 3° 2 Methylamine (a 1° amine) Dimethylamine (a 2° amine) Trimethylamine (a 3° amine) CH 3 -NH 2 CH 3 -NH CH 3 -N CH 3 CH 3 CH 3 : : Aliphatic vs. aromatic Aniline (a 1° aromatic amine) N-Methylaniline (a 2° aromatic amine) B enzyldimethylamine (a 3° aliphatic amine) NH 2 N-H CH 2 -N-CH 3 CH 3 CH 3
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3 Pyrrole Piperidine Pyrrolidine Pyridine (heterocyclic aliphatic amines) (heterocyclic aromatic amines) N N N H H N H Heterocyclic Structure and Classification
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All Amines are Weak Bases 4 H H CH 3 -N H-O-H H H CH 3 -N-H O-H Methylammonium hydroxide Methylamine + + - CH 3 NH 3 + H 2 O CH 3 NH 2 H 3 O + + + [ CH 3 NH 2 ] [H 3 O + ] [CH 3 NH 3 + ] 2.29 x 10 -11 = = K a p K a  = 10.64 it is common to discuss their basicity by reference to the acid ionization constant of the conjugate acid CH 3 NH 2 CH 3 COOH CH 3 NH 3 + CH 3 COO - K eq  = 7.6 x 10 5 + + p K a  10.64 p K a  4.76 (stronger acid) (weaker acid) p K eq  = -5.88
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Basicity of Aliphatic Amines 5 CH 3 NH 2 NH 3 CH 3 CH 2 NH 2 C 6 H 1 1 NH 2 (CH 3 ) 2 NH (CH 3 CH 2 ) 2 NH (CH 3 ) 3
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This note was uploaded on 03/22/2009 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

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Chapter 23-1 - CHEM 262 Wei You Chapter 23 Amines(1 1...

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