Chapter 23-2

Chapter 23-2 - CHEM 262 Wei You Chapter 23. Amines (2) 1...

Info iconThis preview shows pages 1–6. Sign up to view the full content.

View Full Document Right Arrow Icon
1 CHEM 262 Wei You Chapter 23. Amines (2)
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Reaction with HNO 2 2 HNO 2 H 2 O H 3 O + NO 2 - + p K a  = 3.37 + Nitrous acid, a weak acid, is most commonly prepared by treating NaNO 2 with aqueous H 2 SO 4 or HCl In its reactions with amines, nitrous acid participates in proton-transfer reactions is a source of the nitrosyl cation, NO + , a weak electrophile
Background image of page 2
Formation of NO + 3 NO + is formed in the following way – we study the reactions of HNO 2 with 1°, 2°, and 3° aliphatic and aromatic amines H H N O + O H H + O H N O N O O H N O + + + + The nitrosyl cation (1) (2)
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Amines with HNO 2 4 3° aliphatic amines, whether water-soluble or water- insoluble, are protonated to form water-soluble salts 3° aromatic amines: NO + is a weak electrophile and, as such, participates in EAS 2° aliphatic and aromatic amines react with NO + to give N - nitrosoamines Me 2 N 1. NaNO 2 , HCl,  0-5°C 2. NaOH, H 2 O N=O Me 2 N N,N -Dimethyl-4-nitrosoaniline N,N -Dimethylaniline N-H HNO 2 N-N=O H 2 O Piperidine N -Nitrosopiperidine + +
Background image of page 4
Mechanism of 2° amine to N-nitrosamine 5 N H N O N H N=O H O H
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Image of page 6
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 03/22/2009 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

Page1 / 16

Chapter 23-2 - CHEM 262 Wei You Chapter 23. Amines (2) 1...

This preview shows document pages 1 - 6. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online