Exam 3

Question 1

H2

Answer 1

replaces double bond with 2 hs

Question 2

HX

Answer 2

replace double bond with H and X
- looks like substitution

Question 3

H2O2

Answer 3

• antimikov
• places X on least substituted

Question 4

markonicov

Answer 4

• adds H to least and X on most substituted

Question 5

H3O+

Answer 5

gives OH

Question 6

dihydroxylation

Answer 6

OsO4
- cold

Question 7

O3 and H2O2

Answer 7

get 2 =O
1 OH

Question 8

o3

Answer 8

gives = O

Question 9

HBr excess

Answer 9

gives 2 Br

Question 10

H2/Lindlar’s cat

Answer 10

• gives cis 2 hydrogens on each side of double bond

Question 11

Na with NH3 l

Answer 11

Gives double bond with trans Hs

Question 12

KMnO4, OH-, warm, H3O+

Answer 12

Gives = O
and OH

Question 13

o3 and HOAc

Answer 13

breaks at bond and gives half of reaction
- left and right

Question 14

hydration

Answer 14

• H
• OH

Question 15

hydrogenation

Answer 15

• H
• H

Question 16

dihydroxylation

Answer 16

• OH
• OH

Question 17

oxidative cleavage

Answer 17

• O
• O

Question 18

epoxidation

Answer 18

• O

Question 19

Halogenation

Answer 19

• X
• X

Question 20

halohydrin formation

Answer 20

• X
• OH

Question 21

HX addition

Answer 21

• H
• X

Question 22

cyclopropanation

Question 23

HCL

Answer 23

HX
- H less sub and Cl most sub =

Question 24

HBr/ROOR

Answer 24

antimark
- not other roor

Question 25

HOH

Answer 25

• Hydration
• OH on most sub
• look for methyl shift

Question 26

is rearrangement possible on oxymercuration?

Answer 26

no

Question 27

Hg(OAc)2

Answer 27

end with OH, H
- oxymercuration

Question 28

BH2, -THF
H2O2, -OH

Answer 28

anti
- Gives H and OH

Question 29

Br2, Cl2, I2

Answer 29

cis
- anti addition if trans

Question 30

CCl4

Answer 30

solvent

Question 31

Cl2/ H20

Answer 31

gives 1 Cl and OH

Question 32

OH and X

Answer 32

Cl2/H20
- OH on most sub
- halohydrins

Question 33

catalytic hydrogenation of alkenes

Answer 33

use H2 with Ni, Pd, or Pt
- gives wedge or dash

Question 34

both catalytic hydrogenation wedges

Answer 34

syn

Question 35

epoxidation

Answer 35

• CO3H
• opens ring if acidic
• line angle = triangle O
• ring = 2 OH

Question 36

syn dihydroxylation

Answer 36

• gives OH on same side
• OsO4, H2O2
• KMnO4, OH- cold and diluted

Question 37

oxidative cleavage

Answer 37

• KMnO4 warm and conc
• break and replace with = O

Question 38

Warm and Conc

Answer 38

O = and OH

Question 39

O3 in -78
CH3)2S

Answer 39

O = H and H
- O leaves