CnH2n2

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

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

2
???????????????????
?????????? CnH2n-2
3
??????????????? ????????????????????????

• ????????
• ??????????????????????????????????????????????????
  ????????????
• ????????
• ????????????????????????? ????????????????????????
  ?????
• ???????????
• ??????????????????????????????

4

• ?????????????? terminal alkyne (1-alkyne)

5
???????????????? ????????????

• acetylene

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

• 1. Elimination ??? vicinal dihalide

• ??????????? NaNH2 ???? 2 ?????????????????
• ???????????????? terminal alkyne ??????? NaNH2
  ???? 3 ????
• ??? -KOH ??????????? (alcoholic KOH) ,
  heat -NaNH2 ???? LiNH2 ?? NH3

7
(No Transcript)
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• 2. Dehalogenation ??? tetrahalide

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3. Alkylation ??? acetylide ions

• ?????? 2-pentyne ??? 2-pentene
• ?????? 3-octyne ??? 1-butene

10
???????????????????

• Addition

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• 1. Hydrogenation

Lindlars catalystPd/CaCO3 ?????????? Pd/BaSO4
???? Ni2B (P-2) ?????
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• 2. Electrophilic addition
• 2.1 addition of HX

Markovnikov addition
????? peroxide ???? radical addition
gtanti-Markovnikov
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• 2.2 addition of X2

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2.3 addition of H2O
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• 3. Oxidative cleavage

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• 4. Polymerization

17

• ?????????
• ?????????????????????
• (Z)-3-methyl-2-hexen-5-yne
• 4-methyl-2-hexyne
• ????????????????????
• ????????????????????????????????
• 2-hexyne ??? ethyne
• ??? ethyne

18
??????????????????????

• ????????????????????????? 2 ???
• ?????????? CnH2n-2
• ????????????
• cumulative diene
• isolated diene
• conjugated diene

• ?? p-orbital ????????????????????? 4 orbitals
• ??????????????????????????????????????????????????
  ????????
• ????? conjugated diene ????????????? diene
  ????????

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????????? conjugated diene

• 1. Dehydration

2. Dehydrohalogenation
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???????????? conjugated diene

• 1. Electrophilic addition
• 1,2- ??? 1,4-addition

21

• ?????????????

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• Allylic carbocation

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• 2. Diels-Alder reaction 1,4-cycloaddition

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• 3. Polymerization 1,4-addition

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(No Transcript)
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• ???????????? alkynes ??? alkadienes
• ????????? A, B, C ????????????? C6H10
  ??????????? Br2 ?? CCl4 ????????? A
  ????????????????????????? Ag(NH3)2 ???????????
  ??? A ??? B ?????????????? H2 ????? Pt
  ??????????????????????????? n-hexane ??????? C
  ?????????????? H2 1 ??? ??????????????????????
  C6H12 ???????????????? ozonolysis ??? A
  ???????????????? CH3CH2CH2CH2COOH ??? HCOOH ??? B
  ???????????????? CH3CH2COOH ??????????????
  ??????? C ???????????????? ??????????????
• ???????????????????? A, B, C