Chapter 9 Reactions

Question 1

H2, Pt

Answer 1

Hydrogenation

Question 2

Hydrogenation

Answer 2

H2, Pt

Question 2

HX

Answer 2

Reagents for hydrohalogenation (Markovnikov spatial)

Question 2

Br2

Answer 2

Bromination

Question 3

1) BH3•THF 2) H2O2, NaOH

Answer 3

Hydroboration-oxidation

Question 3

Br2, H2O

Answer 3

Halohydrin formation

Question 5

Halohydrin formation

Answer 5

Br2, H2O

Question 6

Acid-catalyzed hydration and oxymercuration-demercuration

Answer 6

H3O+ OR 1) Hg(OAc)2, H2O 2) NaBH4

Question 7

Reagents for hydrohalogenation (Markovnikov spatial)

Answer 7

HX

Question 8

Anti dihydroxylation

Answer 8

1) RCO3H 2) H3O+

Question 9

1) OsO4 2) NaHSO3

Answer 9

Syn dihydroxylation

Question 11

1) RCO3H 2) H3O+

Answer 11

Anti dihydroxylation

Question 12

Hydroboration-oxidation

Answer 12

1) BH3•THF 2) H2O2, NaOH

Question 13

Bromination

Answer 13

Br2

Question 14

Ozonolysis

Answer 14

1) O3 2) DMS

Question 15

1) O3 2) DMS

Answer 15

Ozonolysis

Question 17

HBr, ROOR (peroxide)

Answer 17

Reagents for hydrohalogenation (anti-Markovnikov)

Question 18

H3O+ OR 1) Hg(OAc)2, H2O 2) NaBH4

Answer 18

Acid-catalyzed hydration and oxymercuration-demercuration

Question 19

Syn dihydroxylation

Answer 19

1) OsO4 2) NaHSO3

Question 20

Reagents for hydrohalogenation (anti-Markovnikov)

Answer 20

HBr, ROOR (peroxide)