Oxidation-Reduction Reactions

Question 1

CH4 -(oxidization)->

Answer 1

CH3OH

Question 4

alkene + H2 | Pd/C

Answer 4

alkane

Question 5

ketone + H2NNH2 | HO-, delta

Answer 5

alkane, =O removed (Wolff-Kishner)

Question 6

alkyne + H2 | Pd/C

Answer 6

alkane

Question 7

alkene + H2 | Pd/C

Answer 7

alkane

Question 8

ketone + H2NNH2 | HO-, delta

Answer 8

alkane, =O removed (Wolff-Kishner)

Question 9

alkyne + H2 | Pd/C

Answer 9

alkane

Question 10

C=N + H2 | Pd/C

Answer 10

amine

Question 11

C≡N + H2 | Raney Ni

Answer 11

amine

Question 12

alkyne + Na or Li | NH3 (l)

Answer 12

alkene (trans)

Question 13

ketone + H2 | Raney Ni

Answer 13

secondary alcohol

Question 14

acyl halide + H2 | partially deactivated Pd

Answer 14

aldehyde

Question 15

alkyne + H2 | Lindlar

Answer 15

alkene (cis)

Question 16

alkyne + Na or Li | NH3 (l)

Answer 16

alkene (trans)

Question 17

aldehyde + 1. NaBH4 | 2. H3O+

Answer 17

primary alcohol

Question 18

acyl halide + 1. NaBH4 | 2. H3O+

Answer 18

primary alcohol

Question 19

acyl halide + 1. NaBH4 | 2. H3O+

Answer 19

primary alcohol

Question 20

acyl halide + 1. LiAl[O(t-Bu)]3H, -78 ° C | 2. H2O

Answer 20

aldehyde

Question 21

carboxylic acid + 1. LiAlH4 | 2. H3O+

Answer 21

primary alcohol and water

Question 22

amide + 1. LiAlH4 | 2. H2O

Answer 22

amine (loss of =O)

Question 23

acyl halide + 1. LiAl[O(t-Bu)]3H, -78 ° C | 2. H2O

Answer 23

aldehyde

Question 24

aldehyde + H2 | Raney Ni

Answer 24

primary alcohol

Question 25

ketone + 1. NaBH4 | 2. H3O+

Answer 25

secondary alcohol

Question 26

primary alcohol + H2CrO4

Answer 26

carboxylic acid

Question 27

secondary alcohol + H2CrO4

Answer 27

ketone

Question 28

primary alcohol + PCC | CH2Cl2

Answer 28

aldehyde

Question 29

primary alcohol + 1. DMSO, [COCl]2, -60°C | 2. triethylamine

Answer 29

aldehyde (Swern oxidation)

Question 30

aldehyde + H2CrO4

Answer 30

carboxylic acid

Question 31

aldehyde + 1. Ag2O, NH3 | 2. H3O+

Answer 31

carboxylic acid + metallic silver (Tollens reagent) [only oxidizes aldehydes]

Question 32

cyclohexanone + 50% HNO3

Answer 32

adipic acid (six carbons, dicarboxylic acid)

Question 33

aldehyde + peroxytrifluoroacetate [CF3-(C=O)OO-]

Answer 33

carboxylic acid (Baeyer-Villager reaction)

Question 34

ketone + peroxytrifluoroacetate [CF3-(C=O)OO-]

Answer 34

ester (Baeyer-Villager reaction) (tetrahedral intermediate, plus 1,2-alkyl shift)

Question 35

alkene + 1. OsO4 | 2. H2O2

Answer 35

cis- vicinal diol (formation of cyclic intermediate)

Question 36

1,2-diol + HIO4

Answer 36

cleaved product (via formation of cyclic intermediate with iodine)

Question 37

alkene + 1. O3, -78 ° C | 2. work-up

Answer 37

two carbonyl compounds (intermediate formation of ozonide) (“work-up” is H2O2, Zn+H2O, or DMS)

Question 38

alkene + 1. KMnO4, HO-, H2O (cold)

Answer 38

vicinal diol (probably intermediate?)

Question 39

alkene + KMnO4, HO-, heat

Answer 39

two carbonyl compounds

Question 40

alkene + KMnO4, H+

Answer 40

two carbonyl compounds

Question 41

secondary alcohol + 1. DMSO, [COCl]2, -60°C | 2. triethylamine

Answer 41

ketone (Swern oxidation)