Oganic Chem 221 review

Alkyne -> trans-Alkene

Uses 1 and 2 electron transfers (both single and double headed arrows)

Alkyne -> Alkene Halide

Br adds markovnikov
In excess Br adds geminally (to same carbon)

Alkyne -> Alkene Halide

Halogen adds antimarkovnikovly due to presence of peroxides

Alkyen -> ketone (O=R)

Tautomerization is where the double bond between the two Carbons moves between the Carbon and Oxygen

Alkene -> Alkyl Halide

Br adds markovnikov
Carbocation intermediate
Rearrangements possible
Reacts even at low temps

Alcohol -> Alkene

Carbocation rearrangements possible
Tertiary and Seconday carbons (E1)
Hydronium goes in and comes out

Alcohol -> Alkene

Concerted process (1 step)
E2 Mechanism (primary carbons)

Alkyl Halide -> Alkene

Concerted reaction (1 step)
Primary E2 reaction
B is a base
X is a halogen

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 -> 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

Alkene -> Alcohol

Carbocation rearangements possible
Hydroxyl group adds markovnikov
Hydronium goes in and comes out
Tertiary and secondary substrates (E1)

Alkene -> Alkyl Halide

Antimarkovnikov
No carbocation rearrangements

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 Halide

No change to double bond
Br adds alylically

Alkene -> Alkane

Syn-addition of H's to less hindered face

B adds antimarkovnikov to the double bond
B adds syn-addition to less hinderes face
No carbocation

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 Alcohol

Substitution
Produces a carbocation intermediate; Allylic system
Replaces the halide with a hydroxyl group
Favors markovnikov

Benzene -> Isolated Diene
Markovnikov (meaning if there is a substituent, a double bond will be touching it)

Benzene -> Nitrobenzene
Reaction of nitronium cation with benzene

Benzene -> Sulfonated Benzene