Reaction: All

Question 1

Hydrogenation

Answer 1

AS: H-H or D-D
Reagents: H2 in Pd, Ni, Rh, or Pt
RS: N/A
SS: Syn

Question 2

Hydrohalogenation

Answer 2

AS: H-X
Reagents: H-X
RS: Markov
SS: N/A

Question 3

Hydrobromination in peroxides

Answer 3

AS: H-Br
Reagents: HBr in peroxides (ROOR)
RS: Anti-Markov
SS: N/A

Question 4

Acid-catalyzed hydration

Answer 4

AS: H-OH
Reagents: H+/H2O(acid)
RS: Markov
SS: N/A

Question 5

Oxymercuration-demercuration

Answer 5

AS: H-OH
Reagents: H2SO4, HgSO4, H2O
RS: Markov
SS: N/A

Question 6

Hydroboration-oxidation

Answer 6

AS: H-OH
Reagents: BH3, THF or H2O2, -OH @ room temp
RS: Anti-Markov
SS: Syn

Question 7

Halogenation

Answer 7

AS: X-X
Reagents: X2 in CCl4 (solvent)
RS: N/A
SS: Anti

Question 8

Mixed-Halogenation

Answer 8

AS: X-Y
Reagents: X-Y in CCl4 (solvent)
RS: “Markov”
SS: Anti

Question 9

Halohydrin Formation

Answer 9

AS: X-OH
Reagents: X2 in H2O or NXS in H2O
RS: “Markov”
SS: Anti

Question 10

Dihydroxylation

Answer 10

AS: HO-OH
Reagents: OsO4, NaHSO3, then H2O
RS: N/A
SS: Syn

Question 11

Epoxidation

Answer 11

AS: O
Reagents: RCO3H (peroxyacid)
RS: N/A
SS: Syn