Orgo Exam III

Hydrohalogenation reagents

HX

Hydrohalogenation what gets added

H, X

Hydrohalogenation intermediate

Carbocation

Hydrohalogenation regiochemistry

Markovnikov

Hydrohalogenation Stereochemistry

N/A

Acid Catalyzed Hydration Reagents

H2SO4 / H2O

Acid Catalyzed Hydration What gets added

H, OH

Acid Catalyzed Hydration intermediate

Carbocation + oxonium

Acid Catalyzed Hydration Regiochemistry

Markovnikov

Acid Catalyzed Hydration Stereochemistry

N/A

Halogenation Reagent

X2

Halogenation What gets added

X, X

Halogenation Intermediate

Bridged Halonium ion

Halogenation Regiochemistry

N/A

Halogenation Stereochemistry

Anti

Halohydrin reagents

X2 / H2O

Halohydrin what gets added

X, OH

Halohydrin intermediate

Bridged halonium + oxonium

Halohydrin regiochem

H2O attacks more sub location

Halohydrin Stereochem

anti

Oxymercuration-Reduction reagents

Hg(OAc)2, H20 / NaBH4

Oxymercuration-Reduction what gets added

H, OH

Oxymercuration-Reduction intermediate

Bridged mercurinium ion + oxonium

Oxymercuration-Reduction Regiochem

“markovnikov”

Oxymercuration-Reduction stereochem

anti

Hydroboration Oxidation Reagents

BH3, THF / NaOH, H2O2

Hydroboration Oxidation what gets added

H, OH

Hydroboration Oxidation intermediate

Trisalkylborate (alykyl borate)

Hydroboration Oxidation regio

anti markovnikov

Hydroboration Oxidation stereo

syn

Oxidation to make glycols reagents

OsO4, NMO / NaHSO3

Oxidation to make glycols what gets added

HO, OH

Oxidation to make glycols intermediate

osmate ester (5 membered rings)

Oxidation to make glycols regio

N/A

Oxidation to make glycols stereo

Syn

Ozonolysis reagent

O3 / Me2S

Ozonolysis what gets added

produces two Os that are double bonded to other things

Ozonolysis intermediate

Malozonide ozonide

Ozonolysis Regio

N/A

Ozonolysis stereo

syn due to malozonide

Catalytic Hydrogenation (reduction) reagents

Pd, H2

Catalytic Hydrogenation (reduction) what gets added

H, H

Catalytic Hydrogenation (reduction) intermediate

Pd-bound alkene

Catalytic Hydrogenation (reduction) regio

N/A

Catalytic Hydrogenation (reduction) stereo

Syn