Alkene Reactions

Question 1

Hydrogenation of alkene

Answer 1

H2 and Pd/C
C=C -> C-C

Question 2

Hydrohalogenation of Alkene

Answer 2

H-X
Adds halogen at more substituted C

Question 3

Hydration

Answer 3

H2SO4 and H2O
Adds OH at more substituted C
Regiospecific Markovnikov addition

Question 4

Alkene Isomerization

Answer 4

HSO4
Breaks alkene and then adds it back in a more stable position

Question 5

Halogenation

Answer 5

X-X
Adds 2 halogens
Epoxide intermediate
Stereospecific anti addition of halogens

Question 6

Halohydrin synthesis

Answer 6

X-X and H2O
Adds OH to more substituted C and adds halogen to less substituted C
Epoxide intermediate
Stereospecific anti addition

Question 7

Oxymercuration-Reduction

Answer 7

1. Hg(OAc)2, HOH or HOR 2. NaBH4, NaOH
   Epoxide intermediate with Hg
   Adds OH or OR to more substituted Carbon
   Avoids carbocations

Question 8

Hydroboration-Oxidation

Answer 8

1. BH3 2. H2O2, NaOH
   Epoxide intermediate
   Adds OH to less substituted Carbon and H to more substituted Carbon
   Stereospecific concerted SYN addition
   Regiospecific Anti-Markovnikov addition that avoids carbocations

Question 9

Epoxidation

Answer 9

MCPBA
Stereospecific concerted SYN addition

Question 10

Syn-Dihydroxylation

Answer 10

1. OsO4 2. H2S
   Adds two OH groups on adjacent Carbons
   5 membered ring intermediate

Question 11

Ozonolysis

Answer 11

Reductive workup: 1. O3 2. S(CH3)2
Forms ketone and aldehyde products
Oxidative workup: 1. O3 2. H2O2, H2O
Forms ketone and carboxylic acid products
5 membered ring intermediate