18. Organic III (AMIDES)
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Give the amide functional group
RCONR C is double bonded to O
Give the three different types of amides
Primary amide - 2 hydrogens are attached to the nitrogen - ie RCONH2 Secondary amide - one of the groups attached to the nitrogen is a hydrogen, the other is an alkyl group Tertiary amide - both groups attached to the nitrogen are alkyl groups
Describe how to make a primary amide
Acyl chloride + ammonia —> primary amide + hydrochloric acid Eg: RCOCl + NH3 —> RCONH2 + HCl HCl produced can react with another molecule of NH3 to produce NH4+Cl-
Describe how to make a secondary amide
Acyl chloride + primary amine —> secondary amide + alkyl ammonium chloride Eg: RCOCl + 2RNH2 —> RCONHR + RNH3Cl
Describe how to make a tertiary amide
Acyl chloride + secondary amine —> tertiary amide + alkyl ammonium chloride Eg: ROCl + 2RNHR —> RCONRR + RNH3Cl
What would see when making all types of amides
Misty fumes of HCl
Give the ways in which amides can react
Can undergoes hydrolysis Can undergo reduction
Describe hydrolysis of amides
Reflux either under acidic or aqueous conditions Acidic: RCONH2 + H+ + H2O —> RCOOH + NH4+ Alkaline: RCONH2 + OH- (aq) —> RCOO- + NH3 (acidify with a strong acid to obtain carboxylic acid)
Describe the reduction of amides
Amides can undergo reduction to form amines Warm amide with LiAIH4 in dry ether, then follow with hydrolysis of dilute acid Eg: CH3CONH2 + 4[H] —> CH3CH2NH2 + H2O