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9_alkenes_alkynes_post

9_alkenes_alkynes_post

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Published by: api-3767370 on Oct 16, 2008
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05/09/2014

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Sec. 10 - alkenes/alkynes
1
Addition Reactions to Alkenes
Addition of Hydrogen Halides to Alkenes.
C C
H
H
H
H
R2C=CR2 +HX
R2HC-CR2X
Nucleophile
(weak base)
+ H+
Electrophile
(acid)
C C
H
H
HH
H
+
General Reaction
X
Nucleophile
(base)
Electrophile
(acid)
C C
HH
HH
H
X
Order of reactivity = HI > HBr > HCl > HFWhy?
Slow
Fast

Reactivity parallels acid strength. The
alkene is a very weak base so you need
a very strong acid to get a reaction.

Why?
Unsymmetrical alkene
Sec. 10 - alkenes/alkynes
2
Markovnikov\u2019s Rule

In the ionic addition of an unsymmetrical reagent to a double bond, the positive
portion of the adding reagent attaches itself to a carbon atom to the double bond as
to yield the more stable carbocation as an intermediate (You already knew this from
SN1 reactions. The most stable carbocation intermediate forms)

or
Hydrogen becomes
attached to the carbon
atom of the double
bond with the greater
number of hydrogens

Sec. 10 - alkenes/alkynes
3
Examples
CC
HCH3
H3C
H3C
H Br
+
nucleophile
(weak base)
electrophile
(acid)
CC
H
CH3
H3C
H3C
H
+
CCH2CH3
H3C
H3CBr
sp2
sp2
sp3
sp3
majorpr oduct
CH3
CH3
H Br
+
CH3
CH3
H
H+
CH3
CH3
Br
Br
CH3
CH3
(R)
(R)
(R)
(S)
diastereomers
bottom
top
top
bottom
+

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