Reactions of alkenes and alkynes

YuNi

課本：Organic Chemistry with Biological Approach

2026.06.21 公開

コメントはまだありません。

ノートテキスト

ページ1:

alkene reactions
1. dehydrohalogenation:
4. halohydrin formation:
HBr
(SB)
X₂
KOH
+KBr + H₂O
ex:
TH
C211504
H₂O
H
HO
H
1.14
BY:
2.
dehydration
Bra HC
HBC
Br
H
HBC
Br
ex:
(SA)
+By
-c-c-n →
e
CH3
H3C
CH3 H₂SO4, H₂O
H3C
-H + H₂D
H3C
H
H
-OH
ex:
THF, 50°C
+ H₂O
H
HO
H-O-H
H-D-H
3. halogenation: (addition)
=
Br
|
Br:
→C-ć
Br
"
ex:
cycloalkene
·Br'
Br
Br
④
: Br
G: Br:
Br
(trans)
5. hydration
H20
H250g
H
H
H-C-C →H-C
6. oxymercuration: 1:20
H-O-H
CH3
-CH3 Hg (OAc)2
H₂O
Hg OAc
Hg (OAc)2, H₂O
NaBH4
→h
+130
+
OH
H
H-O-H
CH3
demevcuration
CH3
FOH NaBH9
H
HgoAc
OH

ページ2:

2. mercury (1) catalyzed hydration
keto-enol
tautomerism O
HOHSO4
R-C=C-H
0
P-C-CH3
H9504
Hg so
R-C=C-HR-C=C
→
internal Hg 50
H
R-C=CH
Hg 504
+ H30 H30
R.
H
+H2D
HO
HO
-
alkyne
R-C=C-R' H₂O, HOSD 45 R-C-CHER" + R-CH₂- (C-R' (mixture)
terminal
alkyne
H9504
3. alkyne acidity: terminal alkyne is more acidic (P.103)
4. R-C=C-H
NANH2, NH3
CH3(CH2)2 Br
R-C=C(CH2)2 CH3
R-C=C-H + = NH₂ Na
R-C=C + NH3
e
R-C = C: + CH3(CH2)2 BY → R-C=C(CH2)2 CH3 + B+ e
→R-C-CH2

ページ3:

7. hydroboration/oxidation syn stereochemistry
Concerted! non-Markonikov! no ce intermediate
(0x1-)
BH3
H2D2
THF
H
CH3
H
CH3
H'
CH3
H
CH₂
DH
HO
H
H
H₂B
H
H
H-
8. hydrogenation syn stereochemistry:
H₂ catalyst t
9. oxidation
-epoxidation
synthesis of epoxide from alkene: concerted, x intermediate
syn stereochemistry
H-O
→
C
+
-R
C.
R
epoxide
catalytic: heterogenous: Pt0z. Pd/C 117 Tent C=C) alkene
synthesis of epoxide from halohydrin
CO + H2O + NaCl
凶
e
=DH
H
H2
..上CH3阻和Pd/C結合
H
PA/C
H
NalH
H2O
H
H
Cleavage to C=0
Ozone (0³)
ex:
03
CH2Cl2
1.03
2. Zn, H₂O
C
CH3(CHANCH=CHCCHỌN CÓ CH
FO +
1.03
2.Zn, H₂OT
DMS
Zn
H30+
C= 0 + 0 = C_
-hydroxylation
H
TO
H
Hapt
- another hydroxylation:
H
H
LOH
-H
H
H-O-H
H
H-
CH3
CH₂
0504
NAHS03
OH
H₂O
0
OH
CH3
*CH 3
CH3(CH2M H + HECCH₂M & CH3
trans
H
LOH
H
"OH

ページ4:

- KMn04
CH3(CH2)3 CH=CH₂
-HT09 + 1,2-dio)
CHS
OH
HTD4
H
OH H2O. THF
reactions:
KMn04
H30+
• CH3(CH2)3 &-04 + CO₂
1.
(P.81)
CH3
CH3
H
H
HT04
H2O, THF
°
HO OH
10. Cyclopropane synthesis
e-
(Porbital)
Carbene (sp²) J-phile (2p)
Ŕ'
A
+ CHC13
CI
CI-CH
CI
0.
:DH
CI
Cl
→
H
cl
•C) + KC)
H
CI
Cl
+120
C: +Cl
Cl
H
cl
H
conjugated dienes more stable
:
④
共振
C=C-C-C+HBr → C-C-C=cc-c-c-c
→ C-c-c=c & C-C-C-C
BY (more)
Br
2. Diels-Alder cycloaddition: diene + dienophil has EwG
5-cis
↑
(Can be = )
stereospecific, reactant stereochemistry kept
CO₂CH3
+
☆
♡
OCH3
→
CH3
cis
CO₂CH3
H
trans
CH3
CH3C=CCH3
HC
reactions of alkyne: less reactive
1 addition: HCl. Brz. H₂
Cl
H2O+CH₂C=CCH3 →
H
Br
CH3C=CH
Br2
CH₂C/2
CHBC=CH (形成(C)
BY
H₂
CH3 C=CCH3 Linda C=CH
Catalyst CH3
H
H₂
Pd/C
butane
CH3