What is the structure of the amide funtional group?

The amide functional group consists of a carbonyl (C=O) group adjacent to a nitrogen atom.

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Explain how amides can be classified as primary, secondary or tertiary based on their structure.

  • Primary amides - The nitrogen is bonded to one carbonyl group (C=O) and two hydrogen atoms.
  • Secondary amides - The nitrogen is bonded to one carbonyl group (C=O), one hydrogen atom and one alkyl or aryl group.
  • Tertiary amides - The nitrogen is bonded to one carbonyl group (C=O), and two alkyl or aryl groups.

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What is the mechanism for the reaction above?

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How are primary amides prepared from acyl chlorides?

Amides are prepared by reacting acyl chlorides with ammonia.


For example, ethanamide can be prepared from ethanoyl chloride and ammonia:

CH3COCl + 2NH3 ➔ CH3CONH2 + NH4Cl

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Name the mechanism in the reaction between acyl chlorides and ammonia?

Nucleophilic addition-elimination

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Which nitrogen compounds are stronger bases - amines or amides?

Amines are stronger bases.

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Why are amides weaker bases than amines?

Amides are weaker bases than amines because the lone pair on the nitrogen atom is less available for donation due to the electron-withdrawing effect of the adjacent carbonyl group.

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Describe the reaction of amides with excess aqueous acid.

Amides undergo hydrolysis when refluxed with aqueous acid to produce a carboxylic acid and an ammonium salt.


For example, the reaction of ethanamide with hydrochloric acid produces ethanoic acid and NH4Cl:

CH3CONH2 + H2O +  HCl ➔ CH3COOH + NH4Cl

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Describe the reaction of primary amides with excess aqueous sodium hydroxide.

Primary amides undergo hydrolysis when refluxed with aqueous sodium hydroxide to produce the sodium carboxylate salt and ammonia.


For example, the reaction of ethanamide with sodium hydroxide produces sodium ethanoate and NH3:

CH3CONH2 + NaOH ➔ CH3COONa + NH3

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Describe the reaction of amides with lithium aluminium hydride.

Amides can be reduced to amines by reacting them with lithium aluminum hydride (LiAlH4) in dry ether. The amide group (-CONH2-) is converted to an amine group, (-NH2).


For example, LiAlH4 reduces ethanamide to ethylamine:

CH3CONH2 + 4[H] ➔ CH3CH2NH2 + H2O

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How are secondary amides prepared from acyl chlorides?

Amides are prepared by reacting acyl chlorides with primary amines.


For example, N-methylethanamide can be prepared from ethanoyl chloride and methylamine:

CH3COCl + CH3NH2 ➔ CH3CONHCH3 + HCl

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