Chapter 17 (Lecture #16)

Chapter 17 (Lecture #16) - Amides O RCNHR' 2o = = O RCNH2...

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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 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
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Secondary and Tertiary Amides The reaction of acyl chlorides with primary and secondary amines 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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Amides from Carboxylic Acid Anhydrides Analogous reactions occur between acid anhydrides and ammonia or amines. CH 3 COCCH 3 O = O acetic anhydride + 2 NH 3 CH 3 CNH 2 O + CH 3 CO NH 4 O - + acetamide ammonium acetate by way of CH 3 C-OCCH 3 O O + :NH 3 CH 3 C-N-H O H H + + CH 3 CO 2 - nucleophilic attack at acyl carbon :NH 3 CH 3 CNH 2 O + NH 4 +
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Chapter 17 (Lecture #16) - Amides O RCNHR' 2o = = O RCNH2...

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