??????????? -OH ???????? aromatic ??????

1
403221 ????????????????? ??????????????

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

2
?????????

• ??????????? -OH ???????? aromatic ??????
• ????????????????? -X ???????? aromatic ??????

3

• ????????????????? phenol ???????????????

4
???????????????????????

• ?????
• ???????? 182oC
• ??????????? 43oC
• ???????? 9 ????/100 mL ???
• ?????????????????????????????
• ?????????????????????

5

• ??????????????????????????

• ????????????????

6
??????????????

• 1. Hydrolysis ??? aryl halides

Aryl halide ????????????????????????????????? e-
(strong e- withdrawing)
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• 2. Alkali fusion ???????????? sulfonates

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• 3. ????????? cumene (isopropylbenzene)

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• 4. Hydrolysis ??? diazonium salts

Diazonium salt ????????? aniline
10
?????????????????

• 1. ??????????????????????????

• ????????????????

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• Phenol ????????????????????????????? ?????
  phenolate ion ?? resonance ???????????

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• Phenol ???????????? e- ????????????????????
  Phenol ???????????? e-

• ????????????????????????

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• 2. Ether formation (Williamson synthesis)

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• 3. Ester formation

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• 4. Ring substitution Electrophilic aromatic
  substitution
• -OH activating group o-, p- director
• 4.1 bromination

4.2 nitration
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• 4.3 sulfonation

4.4 Kolbe reaction (OCO) ????????? phenolic
acid
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• 4.5 Reimer-Tiemann reaction
• ????????? phenolic aldehyde

4.6 Coupling ??? diazonium salt ?????? azo dye
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• 4.7 ???????????? formaldehyde

phenol-formaldehyde resin Bakelite
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• 4.8 ??????? phthalein dye

phenolphthalein
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fluorescein
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• 5. ??????????? phenol
• 5.1 phenol ??????????????
• -??????????????? Na2CO3, NaOH
• -?????????????????? NaHCO3
• 5.2 phenol ????????????????????????????, ????,
• ??? ??????????? FeCl3

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

• Aryl halide ????????????? nucleophilic
  substitution ??????? alkyl halide ??????????
  resonance ??????

• ????? C-X ??? Aryl halide ????????????????????????
  ???????????????????? C-X ??? Alkyl halide

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• ????????? nucleophilic aromatic substitution
  (SNAr)
• aryl halide ?????????????????????? ???? -NO2,
  -NO, -CN ?????????? ortho-, para- ??????? -X
  ??????????????????????? Nucleophile ???

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• ????????????? nucleophilic aromatic substitution
  (SNAr)
• ??? addition-elimination

1.
2.
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• Resonance form ??? carbanion ????? carbanion
  ?????????????

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• -aryl halide ?????????????????????????
  ??????????????????????? Nucleophile ????????
  strong base ???? NH2-
• -???????????????????????? elimination-addition

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• ????????????? nucleophilic aromatic substitution
• ??? elimination-addition Benzyne

1.
2.