Ch 12 Reactions

Question 1

Reduction (carbonyl to alcohol)

Answer 1

NaBH4
solvent: MeOH
REMEMBER WORKUP HCl, H2O

Question 2

Jones Oxidation

Answer 2

CrO3, H2SO4, H2O

Question 3

Weak Oxidation

Answer 3

PCC
Solv: DCM

Question 4

Radical Bromination

Answer 4

Br2, hv, CBr4

Question 5

Selective Bromination

Answer 5

PBr3, DCM

Question 6

Hydrogenation

Answer 6

H2
Metal Catalyst (Pd/C)

Question 7

HX Addition carbocation or no?

Answer 7

HX
CARBOCATION

Question 8

Hydration

Answer 8

H2O
H2SO4

Question 9

Isomerization

Answer 9

H2SO4
H2O
HEAT TRIANGLE

Question 10

X2 Addition

Answer 10

X2
Et2O

Question 11

Halonium w/ other nucleophiles

Answer 11

X2
H2O

OH, or other nucleophiles, take priority over X(-)

Question 12

Oxymercuration/Demurcuration

Answer 12

1. Hg(OAc)2, H2O
2. NaBH4, NaOH, H2O

Question 13

Hydroboration - oxidation

Answer 13

1. BH3, THF
2. NaOH, H2O2

Question 14

Regioselectivity of Oxymercuration

Answer 14

NO CARBOCATION
Mark’s Rule
Anti- Addition (Sn2-like inversion)

Question 15

Regioselectivity of Acidic Hydration

Answer 15

CARBOCATION
Most stable carbocation will take alcohol

Question 16

Regioselectivity of Hydroboration

Answer 16

NO CARBOCATION
Anti-Mark’s rule

Question 17

Cyclopropanation w/ Carbenes

Answer 17

Carbene (CH2N2, CCl2)
HEAT TRIANGLE OR hv

Question 18

Epoxidation

Answer 18

mCPBA
DCM

Question 19

Syn Dihydroxylation

Answer 19

1. OsO4, THF
2. H2S

OR

OsO4 (cat) H2O, NMO (reacts multiple times for every alkene)

Question 20

Ozonolysis

Answer 20

1. O3
2. C2S WORKUP

Shears alkene to create two molecules with carbonyls

Question 21

Radical HX

Answer 21

HX (HBr or HCl)
HEAT hv
H2O2