403221 ???????????? ?????????????????????????? (derivatives of carboxylic acid)

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403221 ??????????????????????????????????????
(derivatives of carboxylic acid)

• ??. ??. ??????? ???????
• ??????????? ??????????????
• ??????????????????????

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?????????
acid derivatives Z -Cl acid chloride
-OCOR acid anhydride -NH2 amide
-OR ester
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??????????????????????????????????????

• Acid chloride
• ????????????? acyl ??????? chloride

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• Acid anhydride
• ????????? acid ????????????????????????????? ????
  anhydride

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• Ester
• ????????????????????????????????????
  ??????????????????????????????????????????????
  -ic acid ????????????????????????????????? -ate

????????????????????? alkyl
???????????? ??????????????? alkanoate
Alkyl alkanoate
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• Amide
• ????????? -(o)ic acid ?????????????????????????
  ???? -amide

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• ?????????????????? N ???? N-alkyl ????
  N,N-dialkyl ????????????

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• Nitrile
• ??????????????????? alkane (?????????????????
  nitrile) ??????? nitrile ????
• ????????? -(o)ic acid ????????????????????????????
  ? ???? -onitrile

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???????????????

• ????????
• acid chloride, acid anhydride, ester
  ?????????????????????? aldehyde ???? ketone
  ???????????????????????????
• amide ????????????????????????????????????????????
  ???????
• ???????? (oC)
• CH3COCl acetyl chloride 51
• CH3CONH2 acetamide 221
• C6H5COCl benzoyl chloride 197
• C6H5CONH2 benzamide 290

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• ????????
• ester C2-C5, amide C1-C6 ???????????
• ???????????????????????????????????????????????
• ?????
• volatile ester ????????
• acid chloride ???????????????

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?????????????????????
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1. Acid chlorides

• 1.1. ?????????

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• 1.2. ?????????
• 1.2.1 hydrolysis

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• 1.2.2 ammonolysis

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• 1.2.3 alcoholysis

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• 1.2.4 Friedel-Craft acylation

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2. Acid anhydrides

• 2.1. ?????????
• 2.1.1 ????????? acid chloride

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• 2.1.2 ????????? ketene (H2CCO)
• ?????????????? acetic anhydride

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• 2.1.3 ????????? dicarboxylic acid
• ?????????????? cyclic anhydride ???????????????
  5-6 ?????

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• 2.2. ?????????
• 2.2.1 hydrolysis

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• 2.2.2 ammonolysis

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• 2.2.3 alcoholysis

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3. Esters

• 3.1. ?????????
• 3.1.1 ????????????????????????

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• ?????????????

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• 3.1.2 ????????? acid chloride

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• 3.1.3 ????????? acid anhydride

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• 3.2. ?????????
• 3.2.1 saponification (hydrolysis in base)

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• 3.2.2 transesterification (alcoholysis)

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• 3.2.3 Reduction

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4. Amides

• 4.1. ?????????
• 4.1.1 ??????????????????????????????????????
  ????

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• 4.1.2 ????????? acid chloride

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• 4.1.3 ????????? acid anhydride

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• 4.2. ?????????
• 4.2.1 hydrolysis

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• 4.2.2 Hoffmann degradation

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5. Nitriles ??? isonitriles

• 5.1. ????????? nitrile
• 5.1.1 ?????????????????????

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• 5.1.2 ????????? amide

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• 5.1.3 ???????????????????????????

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• 5.2. ????????? isonitrile
• 5.2.1 ?????????????????????

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• 5.2.2 carbylamine test

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• 5.3. ?????????
• 5.3.1 hydrolysis

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• 5.3.2 reduction