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08-13 - Mass Spectrometry Alkenes to Alcohols.docx
08-13_-_Mass_Spectrometry_Alkenes_to_Alcohols.docx
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08-13 - Mass Spectrometry Alkenes to Alcohols.docx...
08-13_-_Mass_Spectrometry_Alkenes_to_Alcohols.docx-Mass Spectrometry We have a
08-13 - Mass Spectrometry Alkenes t...
08-13_-_Mass_Spectrometry_Alkenes_to_Alcohols.docx-Mass Spectrometry We have a
Page 4
o
Usually electrophiles (positive charge) attack alkene to utilize both electrons of
the π bond
Equilibration
Just react it with some hydrogen, and it’ll break and make a carbocation, then shift and
become more stable (?)
Electrophilic Addition of Halogens to Alkenes
When you react an alkene with Br
2
, the two bromides are on opposite sides (trans)
o
This implies it can’t have a carbocation E1 elimination
What happens is, since the bromide anion has unpaired electrons, AS IT’S forming its
bond with the primary carbon, the would-be carbocation can start forming a bond as well,
so the now Br
-
has to attack from the other side
The bromonium ion can be trapped by their nucleophiles
If you have an unsymmetric starting species, the carbon that gets attacked is the more
substituted carbon
o
Why? This makes no sense with kinetics
o
It happens because the bridge causes partial carbocation, so the one that it attacks
would be the one that’s a more stable carbocation
Takeaway:
o
You can add hydrogen to a double bond and it becomes cis
o
You can add bromine to a double bond and it becomes trans
o
Learned about hydration (and dehydration)
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