2_18 - 2/17/2010 Chapter 17 Amides do not exhibit basic...

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2/17/2010 1 Chapter 17 Amides do not exhibit basic properties in solution like amines because: Electrons not available for hydrogen bonding Electrons are pulled by more electronegative atom in the carbonyl group.
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2/17/2010 2 Amides have high boiling points due to the numerous amide- amide hydrogen bonding possibilities. In many cases, the amide melting point is even higher than the corresponding carboxylic acids. Boiling points of amides: Monosubstituted > Disubstituted > Trisubstituted Boiling Points Reaction of carboxylic acid with ammonia, a primary or a secondary amine produces an amide at elevated temperature. Carboxylic Acid + Amine Amide Remember: Carboxylic Acid + Alcohol Ester
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3 A primary amine produces a secondary amide A secondary amine produces a tertiary amide OH C O R + R NH 2 NH C O R R + H 2 O Acid part Amine part It is often useful to think of the structure of an ester in terms of its “parent” alcohol and acid molecules. Acid
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2_18 - 2/17/2010 Chapter 17 Amides do not exhibit basic...

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