Chapter 9/10: Addition Reactions of Alkenes/ Alkynes

Question 1

1)MCPBA 2)H3O+ with Alkene

Answer 1

Anti-Dihydroxylation
Adds: OH-OH, Trans
Forms epoxide in first step

Question 2

OsO4,NMO OR KMnO4, NaOH, Cold

with Alkene

Answer 2

SYN-Dihydroxylation

Adds: OH-OH Syn

Question 3

1)O3 2)DMS

with Alkene

Answer 3

Oxidative Cleavage

Adds: =O, =O

Question 4

1) O3 2)H2O

with Alkyne

Answer 4

Alkyne: Ozonolysis
Adds: Two carboxylic acids OR 1 carboxylic acid and 1 CO2

Question 5

H2, Pt

with Alkene

Answer 5

Catalytic Hydrogenation
Adds: H-H
Syn, MESO!

Question 6

H2, Lindlars

with Alkyne

Answer 6

Catalytic Hydrogenation
Adds: H-H
Syn
STOPS at alkene for alkynes

Question 7

Na, NH3

with Alkyne

Answer 7

Catalytic Hydrogenation
Adds: H-H
Anti/Trans

Question 8

Dilute H2SO4

with Alkene

Answer 8

Acid-catalyzed Hydration
Adds: H-OH
Racemic Mixture
Markovnikov

Question 9

1)Hg(Oac)2, Nuc-H
2)NaBH4
with Alkene

Answer 9

OxyMercuration-Demurcuration
Adds: Nuc-H OR OH-H
Markovnikov 
-No carbocation rearrangement
-forms epoxide

Question 10

1) BH3.THF
2)H2O2, NaOH
with Alkene

Answer 10

Hydroboration-oxidation
Adds: OH-H
Syn addition (both on same face)
Racemic
Anti-markovnikov

Question 11

H2SO4, H20, HgSO4

with Alkyne

Answer 11

Alkyne: Hydration
ketone
Markovnikov

Question 12

1) 9BBN 2)H2O2, NaOH

with Alkyne

Answer 12

Alkyne: Hydration
Aldehyde
Anti-Markovniko

Question 13

1)NH2,

with Alkyne

Answer 13

Alkylation through Alkynes

-SN2 attacks a alkyl halide