Ch_322b_18.14 - yields secondary and tertiary amides...

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Amides Amides like amines are classified according to the structure around the nitrogen : RCNH 2 O = RCNHR' O = RCNR'R'' O = 1 o 2 o 3 o Synthesis of Amides from Acyl Chlorides The nucleophilic ammonia, and the derived primary and secondary amines, all react rapidly with acyl chlorides to produce amides. For complete reaction, the byproduct HCl must be neutralized. RCCl O = + :NH 3 RC-Cl O H-N-H H - + RC-Cl O H-N-H H - + RC-N-H O = H H + + Cl - RC-N-H O = H H + + :NH 3 RCNH 2 + NH 4 + O = Either excess ammonia or amine, or a tertiary amine such as triethylamine is added to neutralize the HCl.
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Secondary and Tertiary Amides The reaction of acyl chlorides with primary and secondary amines
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Unformatted text preview: yields secondary and tertiary amides, respectively. RCCl O = + 2 R'NH 2 primary amine RCNHR' + R'NH 3 + Cl-O secondary amide an N-substituted amide RCCl O + 2 R'R''NH secondary amine RCNR'R'' + R'R''NH 2 + Cl-O tertiary amide an N,N-disubstituted amide Note: Two equivalents of the amine are required for complete reaction. Tertiary amines react with acyl chlorides to produce salts, not stable amide products. RCCl O + R' 3 N: RCNR' 3 Cl-O + an acylammonium chloride...
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