Orgo 1 addition reactions

Question 1

Syn addition of 2 hydrogens to an alkene

Answer 1

H2; Pd, Pt, Ni

Question 2

syn and anti addition of a hydrogen and halogen to an alkene, markovnikov, carbocation rearrangement

Answer 2

HCl, HBr, HI

Question 3

syn and anti addition of a hydrogen and OH (or other alcohol group) to an alkene, markovnikov, carbocation rearrangement

Answer 3

H3O+, H20 H+, ROH H+

Question 4

Anti addition of two halogens to an alkene, no carbocation rearrangement

Answer 4

Br2, Cl2; CCl4, CHCl3, CH2CL2

Question 5

Anti addition of a halogen and OH to an alkene, no carbocation rearrangement

Answer 5

Cl2, Br2; H2O

Question 6

Syn and anti addition of a hydrogen and OH (or other alcohol group) to an alkene, markovnikov, no carbocation rearrangement

Answer 6

1) Hg(OAc)2, H2O or H3O+ (or alchohol group) 2) NaBH4

Question 7

Syn addition of a hydrogen and OH (or other alcohol group) to an alkene, anti markovnikov, no carbocation rearrangement

Answer 7

1) BH3, THF 2) H2O2, OH -

Question 8

syn and anti addition of a halogen and hydrogen to an alkene, anti markovnikov, no carbocation rearrangement

Answer 8

HBr, H2O2, Hv or heat

Question 9

syn addition of 4 hydrogens to an alkyne

Answer 9

H2; Pd, Pt, Ni

Question 10

syn addition of only 2 hydrogens to an alkyne

Answer 10

H2, Lindar’s Catalyst (Pd, CaCO3)

Question 11

anti addition of only 2 hydrogens to an alkyne

Answer 11

Na (s) free radical; NH3

Question 12

Syna and anti addition of 1 or 2 halogens and 1 or 2 hydrogens, markovnikov, carbocation rearrangement

Answer 12

HBr, HCl, HI

Question 13

anti addition of 2 or 4 halogens to an alkene, no carbocations

Answer 13

Br2, Cl2

Question 14

syn or anti addition of 2 hydrogen and OH to an alkyne, carbocation present, markovnikov, tautomerize

Answer 14

H2O; Hg+2, HSO4 (H3O if not terminal alkyne)

Question 15

syn addition of an OH and a hydrogen to an alkyne, tautomerizes, no favored regiochemistry

Answer 15

1) BH3, THF 2) H2O2, NaOH

Question 16

Anti addition of an OH and a hydrogen to an alkyne, tautomerizes, favors anti markovnikov

Answer 16

1) (Sia)BH 2)H2O2, OH-

Question 17

Switch a hydrogen for a halogen on an alkane

Answer 17

Br2 or Cl2; Hv or heat