403221 ???????????? ??????????????? (carboxylic acid)

1
403221 ??????????????????????????? (carboxylic
acid)

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

2
?????????

• ?????????????? (carboxylic group) -COOH
• ?????????? CnH2nO2

3
??????????????????????????? (carboxylic acid)

• ?????????
• ????????????????????? ?????????? -ic acid
• ???????????????????????? a-, b-, g-, d-

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• ???? IUPAC
• ??????????????????????????????? -COOH
  ?????????????????? alkanoic acid ??????? -COOH
  ?????????????? 1 ????

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• ???? -COOH ????????????????????????????
  -carboxylic acid
• ???????????? -COOH 2 ???? ?????????????? -dioic
  acid

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• ??????????????????????? ????????? anion
  ???????????????????? -ic acid ???? -ate

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

• ????????
• MW ???????? (oC)
• CH3CH2COOH 74 141
• CH3CH2CH2CH2OH 74 118
• ??????????????????????????????????????????????????
  ???????????????????????????? 2 ?????????????
  cyclic dimer

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• ????????
• ????????????????????????????????? (C1-C4)
  ???????????????????????????????????????
• ???????????????????? C ??????? 6 ????????????????
• ???????????????????????????????

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• ?????
• ??????????????? C1-C3 ???????? ???????
• ??????????????? C4-C6 ??????????
• ??????????????????????????????????????????????????
  ?????????????????????????????

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

• 1. ????????? oxidation ??? 1o alcohol ????
  aldehyde

???????????????????????????? C ?????????????????
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• 2. ????????? oxidation ??? alkylbenzene

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• 3. ????????? carbonation ??? Grignard reagent

???????????????????????????? C ?????????????????
1 ?????
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• 4. ????????? hydrolysis ??? nitrile

???????????????????????????? C ?????????????????
RX 1 ?????
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???????????????????????????

• 1. Salt formation, acidity

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• Carboxlylate ion ????????????? resonance

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• ?????????????????????????????

Ka RCOO-H/RCOOH
Ka HCOOH 17.7 10-5 CH3COOH
1.8 10-5 ClCH2COOH 136.0 10-5
????????????????? ????? anion ?????????? ????????
????????
????????????????? ????? anion ????????? ??????????
???
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• 2. Conversion into functional derivatives

acid derivatives Z -Cl acid chloride
-OR ester -NH2 amide
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• 2.1. Acid chlorides

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• 2.2. Esters

Reactivity ROH 1o gt 2o (gt 3o) RCOOH HCOOHgtCH3C
OOHgtRCH2COOHgtR2CHCOOH
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• 2.3. Amides

?????? carboxylic acid ?????????????? ammonia
????????????????? RCOO-NH4
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• 3. ???????????? diazomethane (CH2N2)

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• 4. ????????? reduction

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• 5. ????????????????????? alkyl ???? aryl
  ??????????????????
• 5.1 a-halogenation ??? aliphatic acid

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• 5.2 ring substitution ??? aromatic acid
• electrophilic aromatic substitution

-COOH deactivating, m- director group