Ch. 8
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Why is a pi bond less stable
The electron density is above and below the C, which is further from the nucleus and less stable
____ bonds are more stable than pi bonds. ______ bonds will break down to sigma bonds
Sigma/single Double
Electrophilic Additions
An addition in which the electrophile bonds to one of the double-bonded carbon first, followed by the nucleophile
Electrophilic Addition mechanism
The pi bond attacks the electrophile to form a carbocation. A nucleophile attacks the carbocation
Markovnikov’s Rule
for an electrophilic addition to the alkene, the electrophile adds in such a way as to generate the most stable intermediate
Anti-Markovnikov Product
an orientation that is the opposite of that predicted by the original statement of Markovnikov Rule
When does the anti-Markovnikov Product
Only works with HBr in the presence of peroxide
How do you form radicals from ROOR
R-O. and .O-R with heat
In Free-Radical addition, the radical on the _____ substituted carbon
more
How does addition of water work
It dilutes the acid to force equilibrium with the alcohol
What is hydroboration?
the addition of borane or one of it’s derivatives to a molecule
Is BH3 a strong electrophile or strong nucleophile?
Strong electrophile
Does hydroboration-oxidation do markovnikov or anti-markovnikov
anti-markovniov
What is halohydrin?
Alcohol with a halogen on the adjacent carbon. Must have a good nucleophile presence like water
Enantioselective Synthesis
the formation of an optically active product from an optically inactive starting material.
What does enantioselective synthesis require
the use of an optically active reagent or catalyst
Carbene
a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons
Acid-Catalyzed Opening of Epoxides
Acid catalyzed reaction, water attacks the protonated epoxide and forms an anti-diol
Hydroxylation
the addition of two hydroxyl groups, one at each carbon of the double bond