(STM)

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13? ????
?????????
??????
??????????? (STM)
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(No Transcript)
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13-1 ???????
alkyne
alkane
????IUPAC?
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??
???? OH
???? ????
?
?
?
?
?
?
?
?
?
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13-2 ??????????
(1) ?? ???????????????????(????????) (2)
???-84????(2-?????27 ?) (3) ????????
?????????(???????) (4) ????????? (5)
?????????? (6) ?????????????????
4p ??
sp????p??
???
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DDH 83
DDH 56
DH 311 / 26 12 kcal/molg (3??gt2500?)
DH 530.6 / 44 12 kcal/molg (7??)
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DDH -4.8
hyperconjugation
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Hydrogensget more acidic (blue) ????????(?)
????????? alkynyl anion ? ?? ? ???
? ?? ? ????
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13-4 ?????????????????
(1) ??????????? 3 ??? NaNH2 ???(2???????) (2)
??????????????????????(??????????)
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B-
??
????
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(No Transcript)
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13-5 ???????????????????
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(No Transcript)
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13-6 ??????? ???p??????????
??? A?B ???????????
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????????????????????
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???????????????????????
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13-7 ????????????
????????????? ??????? ???????????? ???
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?????????????????? Markovnikov ????
?????2????
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???????(II)?????????????????
??????????????
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13-8 ??????? Markovnikov ????
HBr????????????1-???????????
????????????????
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?????????
??????13-1
??
SN2
1-bromo-1-decanol
11-tetradecin-1-ol
???
Na, liq. NH3
trans-11-tetradecen-1-ol
PCC, CH2Cl2
???????????? ???????
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?????????????? ? ?? ???????
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13-9 ????????????????
???????? (???????)
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(No Transcript)
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13-10 ???????????
?????????????
D
?????????????
H2O ? ROH, RNH2 ? ????,???
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(No Transcript)
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13-11 ????????????????
??????
1826 ?????????
??
????? ?????
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?????
????????
????? ???,???
????????
???????
???????? ?????
???????? ???????? ???
????,????? ?????