Reaction

Question 1

Halogenation

Answer 1

Anti addition of X2 -> Nonpolar solvent

Anti addition on cyclic and trans alkene
Syn addition on cis alkene

Question 2

Halohydrin?

Answer 2

Anti addition of X2 -> H2O

OH on more substituted carbon
X on less substituted carbon

Question 3

Acid Catalyzed Hydration

Answer 3

Anti addition of H2O -> Acid

OH on more substituted carbon
H on less substituted carbon

Question 4

Oxymercuration-Demercuration

Answer 4

Anti addition of HgOAc 2, H2O -> NaBH4

OH on more substituted carbon
H on less substituted carbon

Question 5

Hydroboration

Answer 5

Syn Addition of BH3 -> H2O2, NaOH

Anti-Markovnikov
OH on less substituted carbon
H on more substituted carbon

Question 6

Hydrogenation

Answer 6

Syn addition of H2 -> Pd/C

Question 7

Epoxidation via peroxyacids

Answer 7

Syn addition of mCPBA (RCO3H)

Cis alkene gives syn R group
Trans alkene gives anti R group

Question 8

Epxodiation via Bromohydrin’s reaction with base

Answer 8

X2, H2O -> NaOH or NaH

1. Halohydrin
2. React halohydrin product with a base

Syn addition

Question 9

Anti-Dihydroxylation via Acid-Catalyzed Hydrolysis of an Epoxide

Answer 9

mCPBA -> Acid

1. Epoxidation via mCPBA
2. Acid Catalyzed Hydration

Anti Dihydroxylation (2 opposite alcohol)

Question 10

Syn-Dihydroxylation via reaction with OsO4 or KMnO4

Answer 10

OsO4 (or KMnO4) -> NaHSO3, H2O

Syn addition 2 OH using

OsO4, NaHSO3, H2O