Exam 2

Question 1

KMnO4

Answer 1

-ozonolysis,
except H—>OH
-terminal alkenes form carboxylic acid and ketones

Question 2

CH2I2, Zn(Cu)

Answer 2

-Simmons smith rxn
- forms cyclopropane ring
-follows cis/trans from reactant

Question 3

Hg(OAc)2, H2O; then NaBH4

Answer 3

-oxymercuration
-follows markov rule
-trans
-adds OH + H

Question 4

OsO4; then NaHSO3

Answer 4

-adds 2 OH
-Syn
-results in 1,2-diol
-opposite of epoxidation (mcpba)

Question 5

BH3, then H2O2, OH-

Answer 5

-anti markov
-syn
- OH + H

Question 6

O3, then Zn, H3O

Answer 6

-splits double bond and adds O to each end of double bond

Question 7

H2SO4

Answer 7

-alkenes: takes away OH
-alkynes: results in a ketone

Question 8

Cl2

Answer 8

Cl added to each end of double bond
- trans

Question 9

mcpba, then H3O+

Answer 9

-mcpba turns double bond into an epoxy ring
-follows cis/ trans from reactant
-H3O+ opens ring, adds 2 OH trans
-opposite of OsO4

Question 10

Br2, H2O

Answer 10

-halohydrins
-trans addition of OH and X
-OH on more substituted C

Question 11

H3O+

Answer 11

-follows markovinov rule
-create 2°C first, then perform 1,2 hydride shift

Question 12

H2, Pd/C

Answer 12

-syn addition of hydrogens