Alkene Rxns

Question 1

Hydrohalgogenation (v.1)

Answer 1

Adds H and X [X = Cl, Br, I]
Reactant(s) = HCl, HBr, HI
Markovnikov = H less substituted
No stereoisomerism (racemic, mix of syn- and anti-)

Question 2

Hydration + Hydration w/ Rearrangement (acid-catalyzed)

Answer 2

Adds H and OH
Reactant(s) = acids(HSO4) or H3O
Markovnikov = H less substituted
No stereoisomerism (racemic, both syn and anti)

Question 3

Addition of Alcohol (acid-catalyzed alcohol addition)

Answer 3

Adds H and OR
Reactants = H2SO4 (H+) / ROH
Markovnikov = H less substituted
No stereoisomerism (racemic, mix of syn- and anti-)

Question 4

Bromination (form of Halogenation)

Answer 4

Adds Br + Br (X + X)
Reactants = Br2 / solvent (CCl4 or CH2Cl2)
No regio-isomerism
Anti stereoisomerism (dash + wedge)

Question 5

Bromination in H2O (form of Halohydrin Formation)

Answer 5

Adds Br (X) + OH
Reactants = Br2 / H2O
Markovnikov = Br (X) placed on less substituted side
Anti (dash + wedge)

Question 6

Bromination in Alcohol (form of Halohydrin Formation)

Answer 6

Add Groups: Br (X) + OR
Reactants = Br2 / ROH
Markovnikov = Br (X) placed on less substituted side
Anti stereoisomerism (dash + wedge)

Question 7

Oxymercuration-Demercuration (form of Hydration)

Answer 7

Groups Added: H + OH
Reactants = 1. Hg(OAc)2, H2O;
2. NaBH4
Markovnikov = H less substituted
Anti stereochemistry
No rearrangement + creation of mercurium ion

Question 8

Hydroboration Oxidation (form of Hydration)

Answer 8

Groups Added = H + OH
Reactants = 1.BH3 • THF
2. H2O2, NaOH
Anti-Markovnikov = H more substituted
Syn Stereochemistry
Trialkylborane

Question 9

Alkoxymercuration Demurcuration (form of addition of an alcohol)

Answer 9

Groups Added = H + OR (alcohol)
Reactants = 1. Hg(OAc)2, ROH
2. NaBH4
Markovnikov = H less substituted
Anti Stereochemistry
Mercurinium ion intermediate

Question 10

Catalyst Hydrogenation

Answer 10

Groups Added = H + H
Reactants = H2/catalyst
Catalyst = Pd, Pt, Ni
No regiochemistry
Syn stereochemistry

Question 11

Halogenation

Answer 11

Groups Added = X + X
Reactants = X2/solvent
Solvent = CCl4 or CH2Cl2
No regiochemistry
Anti stereochemistry

Question 12

Halohydrin Formation

Answer 12

Groups Added = X + OH/OR
Reactants = X2/H2O or ROH
Markovnikov = X less substituted
Anti stereochemistry

Question 13

Epoxidation

Answer 13

Group Added = O
Reactants = peroxiacid or RCO3H or MCPBA
No regiochemistry
Syn stereochemistry

Question 14

Anti-Dihydroxylation

Answer 14

Groups Added = OH + OH
Reactants = 1. RCO3H/MCPBA
2. H3O+
No regiochemistry
Anti stereochemistry

Question 15

Syn-Dihydroxylstion (v.1)

Answer 15

Groups Added = OH + OH
Reactants = 1. OsO4
2. NaHSO3 or Na2SO3
No regiochemistry
Syn stereochemistry
Cyclic osmate ester

Question 16

Syn-Dihydroxylation (v.2)

Answer 16

Groups Added = OH + OH
Reactants = 1. KMnO4 (cold, dil)
2. NaOH
No regiochemistry
Syn stereochemistry
Cyclic manganate Ester

Question 17

Hydrohalogenation (v.2)

Answer 17

Groups Added = H + Br
Reactants = HBr/HOOH (peroxide)
Anti-Markovnikov = H more substituted
No stereochemistry