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21 Cards in this Set

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Alkyne -> trans-Alkene

Uses 1 and 2 electron transfers (both single and double headed arrows)
Alkyne
Alkyne -> Alkene Halide

Br adds markovnikov
In excess Br adds geminally (to same carbon)
Alkyne
Alkyne -> Alkene Halide

Halogen adds antimarkovnikovly due to presence of peroxides
H2O + H30+
Alkyen -> ketone (O=R)

Tautomerization is where the double bond between the two Carbons moves between the Carbon and Oxygen
Alkene
Alkene -> Alkyl Halide

Br adds markovnikov
Carbocation intermediate
Rearrangements possible
Reacts even at low temps
alkane
Alcohol -> Alkene

Carbocation rearrangements possible
Tertiary and Seconday carbons (E1)
Hydronium goes in and comes out
Alkane
Alcohol -> Alkene

Concerted process (1 step)
E2 Mechanism (primary carbons)
Alcohol starter
Alkane
Alkyl Halide -> Alkene

Concerted reaction (1 step)
Primary E2 reaction
B is a base
X is a halogen
alykyl halide starter
Alkene
Alkene -> Alcohol Halide Alkane

OH goes to more substituated end of double bond
Bromonium ion intermediate
Br and OH add trans/anti-addition vicinally (on adjacent carbons)
The more substituted the double bond, the faster the reaction
alkene
Alkene -> Alkyl Vicinal Dihalide

First Br adds antimarkovnikov to form bromonium ion
Br's add trans and anti-addition and vicinally
The more substituted the double bond, the faster the reaction
alkane
Alkene -> Alcohol

Carbocation rearangements possible
Hydroxyl group adds markovnikov
Hydronium goes in and comes out
Tertiary and secondary substrates (E1)
Alkene
Alkene -> Alkyl Halide

Antimarkovnikov
No carbocation rearrangements
Alkene
Alkene -> Epoxide

O adds syn-addition to less hindered face
No regeoselectivity
No carbocation
The more substituted the double bond the faster the reaction
*O has a bond to each of the carbons that partook in the double bond*
Hexene
Hexene -> Hexene Halide

No change to double bond
Br adds alylically
Alkene
Alkene -> Alkane

Syn-addition of H's to less hindered face
Alkene
B adds antimarkovnikov to the double bond
B adds syn-addition to less hinderes face
No carbocation
Diels Alder Reaction
Cis ring fuse
The substituents on the same side (R vs L) of the double bond being attacked go to the same face one the ring formed (wedge vs dash)
Alkene Halide
Alkene Halide -> Alkene Alcohol

Substitution
Produces a carbocation intermediate; Allylic system
Replaces the halide with a hydroxyl group
Favors markovnikov
Benzene
"Birch Reduction"
Benzene -> Isolated Diene
Markovnikov (meaning if there is a substituent, a double bond will be touching it)
Nitration
Benzene
Benzene -> Nitrobenzene
Reaction of nitronium cation with benzene
Sulfonation
Benzen
Benzene -> Sulfonated Benzene