Orgo midterm 3

what groups does halogenation add?

X₂

what is the regiochemistry of halogenation

no regiochemistry

what, if any, is the stereochemistry of halogenation?

stereospecific for anti

does halogenation produce a racemic mixture?

yes!

are rearrangements possible in halogenation?

no

what are the reagents used in halogenation?

X₂, nonpolar, aprotic solvent (CCl₄)

what groups does Oxymercuration-demercuration add?

H and OH

what is the regiochemistry of oxymercuration-demercuration?

markovnikov

what, if any, is the stereochemistry of oxymercuration-demercuration?

stereospecific for anti

does oxymercuration-demercuration produce a racemic mixture?

yes

are rearrangements possible in oxymercuration-demercuration?

no

what are the reagents used in oxymercuration-demercuration?

Hg(OA_c)₂ which becomes Hg(OA_c) and ^-OA_c and H₂O, then in the second step it uses H₂O and NaOH

what groups does acid-catalyzed hydration add?

H and OH

what is the regiochemistry of acid-catalyzed hydration?

markovnikov

what, if any, is the stereochemistry of acid-catalyzed hydration?

Not stereoselective, no carbocation

does acid-catalyzed hydration produce a racemic mixture?

yes

are rearrangements possible in acid-catalyzed hydration?

yes

what are the reagents used in acid-catalyzed hydration?

A strong acid (H2SO4, TsOH, H3O+), H2O as solvent

what groups does hydroboration-oxidation add?

H and OH

what is the regiochemistry of hydroboration-oxidation?

anti-markovnikov

what, if any, is the stereochemistry of hydroboration-oxidation?

stereospecific for syn

does hydroboration-oxidation produce a racemic mixture?

yes

are rearrangements possible in hydroboration-oxidation?

no

what are the reagents used in hydroboration-oxidation?

BH3, THF, H2O2, NaOH

what groups does anti-markovnikov addition of HBr add?

H and Br

what is the regiochemistry of anti-markovnikov addition of HBr?

anti-markovnikov

what, if any, is the stereochemistry of anti-markovnikov addition of HBr?

not stereoselective

does anti-markovnikov addition of HBr produce a racemic mixture?

yes

Is rearrangement possible in anti-markovnikov addition of HBr?

no

What are the reagents in anti-markovnikov addition of HBr?

HBr and ROOR

What groups are added in hydrohalogenation?

H and X (X=Cl, Br, I)

what is the regiochemistry of hydrohalogenation?

markovnikov

what, if any, is the stereochemistry of hydrohalogenation?

Not stereoselective

does hydrohalogenation produce a racemic mixture?

yes

is rearrangement possible in hydrohalogenation?

yes

what are the reagents used in hydrohalogenation?

H-X (x=cl, br, i), nonpolar, aprotic solvent (CCl4)

what are the groups added in halohydren formation?

OH and X

what is the regiochemistry of halohydren formation?

markovnikov

what, if any, is the stereochemistry of halohydren formation?

stereospecific for anti

does halohydren formation produce a racemic mixture?

yes

are rearrangements possible in halohydren formation?

no

what are the reagents involved in halohydren formation?

X2 and polar, protic solvents like H2O or ROH

what groups are added in hydrogenation?

H2

what is the regiochemistry of Hydrogenation?

no regiochem

what, if any, is the stereochemistry of hydrogenation?

Stereospecific for syn

does hydrogenation produce racemic mixtures?

yes

are rearrangments possible in hydrogenation?

no

what reagents are needed for hydrogenation?

H2, metal catalysts like Pd, Pt, or Ni

what groups are added in racemic epoxidation?

an O

what is the regiochemistry of racemic epoxidation?

none

what, if any, is the stereochemistry of racemic epoxidation?

stereospecific for syn

does racemic epoxidation produce racemic mixtures?

yes

are rearrangements possible in racemic epoxidation?

no

what reagents are used in racemic epoxidation?

mCPBA, or H2O, NaNH2, and Br2

what groups are added in enantioselective epoxidation?

one O

what is the regiochemistry of enantioselective epoxidation?

none

what, if any, is the stereochemistry of enantioselective epoxidation?

stereospecific for syn

does enantioselective epoxidation produce a racemic mixture?

no

are rearrangements possible in enantioselective epoxidation?

no

what reagents are used in enantioselective epoxidation?

jacobs catalyst and NaOCl

what groups are added in epoxide opening?

2 OH groups

what is the regiochemistry of epoxide opening?

none

what is the stereochemistry of epoxide opening?

stereospecific for anti

does epoxide opening create racemic mixtures?

no, OA

are rearrangements possible in epoxide opening?

no

what are the reagents used in epoxide opening?

epoxide, H3O+, H2O

what are the groups added in dihydroxylation?

2 OH groups

what is the regiochemistry of dihydroxylation?

none

what is the stereochemistry of dihydroxylation?

stereospecific for syn

does dihydroxylation produce racemic mixture?

yes

is rearrangement possible with dihydroxylation?

no

what are the reagents used in dihydroxylation?

OSO4, H2O2

is ozonolysis OA or OI

OI

what are the reagents for reductive workup ozonolysis?

O3, -78C, Me2 or NaHSO3

what are the reagents for oxidative workup ozonolysis

O3, -78C, H2O2

what is special about oxidative workup ozonolysis?

it adds a O to the beta hydrogen, creating a carboxylic acid