Alkene Reactions Review

Question 1

HBr (or Cl)

Answer 1

Adds a halide to the more substituted carbon

Question 2

HBr (Cl), ROOR (peroxide)

Answer 2

Adds a halide to the less substituted carbon

Question 3

H2SO4 & H20 (or H3O+)

Answer 3

Adds an oxygen to the more substituted carbon

Question 4

1. Hg(OAc)2, nuc-H
2. NaBH4

Answer 4

Adds an oxygen to the more substituted carbon

Question 5

1. BH3, THF
2. H2O2, NaOH

Answer 5

Adds an oxygen on the less substituted carbon

Question 6

Br2 or Cl2

Answer 6

Adds 2 bromine/chlorine anti across carbon-carbon bond

Question 7

RCO3H & H3O+
OR
MCPBA & H3O+

Answer 7

Anti addition of oxygen across the carbon-carbon bond

Question 8

OsO4 & Na2SO3/H2O
OR
OsO4 & NaHSO3/H2O
OR
KMnO4 (cold) & NaOH

Answer 8

Syn addition of oxygens across a carbon-carbon bond

Question 9

O3 & DMS (or Zn/H2O)

Answer 9

Cleaves the double bond to form two carbonyls