Chapter 12

Question 1

H2 and Metal Catalyst Pd-C

Answer 1

Alkene to Alkane
Syn addition

Question 2

H2 and Lindlar Catalyst

Answer 2

Lindlar= Pd-CaCO3 or Pb(OCOCH3) + quinoline
Alkyne to Alkene
Syn addition

Question 3

Na NH3

Answer 3

Alkyne to Alkene
Anti addition

Question 4

1) LiAlH4
2)H2O
(Alkyl Halide)

Answer 4

Alkyl Halides to Alkane
SN2 Mechanism

Question 5

1) LiAlH4
2)H2O

Answer 5

Epoxide to alcohol
Anti addition
SN2
Can also use NaBH4

Question 6

Primary Alcohol Oxidation

Answer 6

Alcohol to aldehyde or carboxylic acid (only if in H2O)

Oxidants: CrO3, K2Cr2O7 or Na2Cr2O7 (in H2SO4)
, PCC (organic solute)

Question 7

Secondary Alcohol Oxidation

Answer 7

Alcohol to Ketone

Question 8

Tertiary Alcohol Oxidation

Answer 8

No Reaction

Question 9

mCPBA or RCO3H

Answer 9

Alkene to epoxide

Question 10

mCPBA or RCO3H +H2O (OH-)

Answer 10

Alkene to Diol
Anti addition

Question 11

1) Br2 + H2O
2) NaH

Answer 11

Alkene to Epoxide
Halogenated Alcohol intermediary

Question 12

1) KMnO4
2) H2O, OH-

Answer 12

Alkene to diol
Syn addition

Question 13

1) OsO4
2) NaHSO3, H2O

Answer 13

Alkene to diol
Syn addition

Question 14

1) O3
2) Zn, H2O

Answer 14

Alkene splits along double bond. Two compounds formed with new double bonds to oxygen.

Question 15

1) O3
2) CH3SCH3

Answer 15

Alkene splits along double bond, two compounds formed with new double bonds to oxygen.

Question 16

Internal Alkyne Ozonolysis

Answer 16

1) O3
2) H2O
Results in two carboxylic acids

Question 17

Terminal Alkyne Ozonolysis

Answer 17

1) O3
2)H2O
Results in one carboxylic acid and carbon dioxide

Question 18

Alkene to Alkane
Syn addition

Answer 18

H2 and Metal Catalyst Pd-C

Question 19

Lindlar= Pd-CaCO3 or Pb(OCOCH3) + quinoline
Alkyne to Alkene
Syn addition

Answer 19

H2 and Lindlar Catalyst

Question 20

Alkyne to Alkene
Anti addition

Answer 20

Na NH3

Question 21

Alkyl Halides to Alkane
SN2 Mechanism

Answer 21

1) LiAlH4
2)H2O
(Alkyl Halide)

Question 22

Epoxide to alcohol
Anti addition
SN2
Can also use NaBH4

Answer 22

1) LiAlH4
2)H2O

Question 23

Alcohol to aldehyde or carboxylic acid (only if in H2O)

Oxidants: CrO3, K2Cr2O7 or Na2Cr2O7, PCC (organic solute)

Answer 23

Primary Alcohol Oxidation

Question 24

Alcohol to Ketone

Answer 24

Secondary Alcohol Oxidation

Question 25

No Reaction

Answer 25

Tertiary Alcohol Oxidation

Question 26

Alkene to epoxide

Answer 26

mCPBA or RCO3H

Question 27

Alkene to Diol Anti addition

Answer 27

mCPBA or RCO3H +H2O (OH-)

Question 28

Alkene to Epoxide Halogenated Alcohol intermediary

Answer 28

1) Br2 + H2O 2) NaH

Question 29

Alkene to diol Syn addition

Answer 29

1) KMnO4 2) H2O, OH-

Question 30

Alkene to diol Syn addition

Answer 30

1) OsO4 2) NaHSO3, H2O

Question 31

Alkene splits along double bond. Two compounds formed with new double bonds to oxygen.

Answer 31

1) O3 2) Zn, H2O

Question 32

Alkene splits along double bond, two compounds formed with new double bonds to oxygen.

Answer 32

1) O3 2) CH3SCH3

Question 33

1) O3 2) H2O Results in two carboxylic acids

Answer 33

Internal Alkyne Ozonolysis

Question 34

1) O3 2)H2O Results in one carboxylic acid and carbon dioxide

Answer 34

Terminal Alkyne Ozonolysis

Question 35

Alkyl Halide to Alkene

Answer 35

Elimination KOC(CH3)3

Question 36

KOC(CH3)3

Answer 36

Alkyl Halide to Alkene E2 Mechanism