Undergraduate
自然科學

Alkenes and alkynes

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YuNi

YuNi

課本:Organic Chemistry with Biological Approach

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ページ1:

不飽和度:1. basic :
Cx2 H+2
= ⇒ |
2.有鹵: C2-CH+)+2
2
3.有0:0不算
4. AN
C2-CH-N)+2
2
cyclohexane |
cyclohexene | + |=2
2
benzene
13+1 = 4
①
op
1. methylene group
(P.14)
2. vinyl group
3. allyl group
alkene 1. cis-trans: E/Z (according to atomic number)
Ch51.34
can be
found by
- stability: trans> cis ( steric strain)
E
Z
H2
alkane
hydrogenation: alkene Ha
DGT, isomer E↑ (unstable)
E↑
cis
4G cis
trans
2. substitution, stability ↑ (P.31)
hyper conjugation: C=C empty p orbital
bond strength sp²-sp³ > sp³- sp³
(見:34)
C-H bond e
2017
C-C-C
00
CH3-C=C-C3H7
|
|
HH
same number of
substituent (P.44)
3. electrophilic addition (P.36 ~ P.39)
{regiospecific: only one occurs
vegioselective mixture of products results
ex: Markonikov's rule: X more substituenty
Hless
4. Why Markonikov works?
substitution T, C® stability I
inductive effect alkyl group is EDG give c® e¯
hyperconjugation

ページ2:

Hammond Postulate
AOC intermediate stable, rate ↑ (lower E transition state)
(a)
Slower
reaction
Less
stable
intermediate
Faster
reaction
More
stable
intermediate
Reaction progress
*
structure of transition state nearest stable species
endergonic closer to product
exergonic closer to reactant
Any factor that stabilizes the carbocation should also
stabilize the nearby transition state
@
intermediate with co 要考慮!
6.00
rearrangement
hydride (H) shift
alkyl shift group, PT
}₂
more stable Co
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