Lecture26outline

Lecture26outline - I Review Secondary amides do not show multiple signals in the 1H NMR because of the strong thermodynamic preference for the

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
I. Review • Secondary amides do not show multiple signals in the 1 H NMR because of the strong thermodynamic preference for the alkyl groups to have a trans -relationship • Amides are the most stable carboxylic acid derivatives, making them suitable for linkages between amino acids in proteins • Amides have been shown to have a half-life of approximately 7 years at room temperature and neutral pH through a clever experiment that utilized polymer immobilization and kinetic analysis by determining radioactivity increases as a function of time • Amides can be hydrolyzed to carboxylic acids using either acid or base, but high temperatures are required • Tertiary amides react with DIBAL to yield aldehydes because of the stable tetrahedral intermediate that arises from the poor leaving group • Amides react with LiAlH 4 to yield amines because the oxygen, coordinated to both Al and Li, leaves in preference to the nitrogen when the tetrahedral intermediate collapses, forming an iminium ion that is readily reduced
Background image of page 1

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

View Full DocumentRight Arrow Icon
Image of page 2
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 05/17/2010 for the course CHEM 0740 taught by Professor Professor during the Spring '10 term at Pittsburgh.

Page1 / 2

Lecture26outline - I Review Secondary amides do not show multiple signals in the 1H NMR because of the strong thermodynamic preference for the

This preview shows document pages 1 - 2. Sign up to view the full document.

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