Alkene Addition Flashcards by Heather Bryant

Q

halohydrin adds what

A

X + OH

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Q

halohydrin regiochem

A

markovnikov

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Q

halohydrin stereochem

A

anti addition

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Q

halohydrin intermediate

A

bromonium or chloroinuium ion

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Q

halohydrin reagent

A

X2/H20

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Q

epoxidation does what

A

3 membered ring with o

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Q

epoxidation reagent

A

MCPBA or RCO3H

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Q

epoxidation stereochem

A

syn addition and flip products upside down

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Q

anti-dihydroxylation adds what

A

OH + OH

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Q

anti-dihydroxylation stereochem

A

anti addition

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Q

anti-dihydroxylation reagent

A

RCO3H or MCPBA / H3O+, H20

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Q

Acid-catalyzed hydration adds what

A

H + OH

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Q

acid-catalyzed hydration regiochem

A

Markovnikov

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Q

acid-catalyzed hydration stereochem

A

all

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Q

acid-catalyzed hydration intermediate

A

carbocation

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Q

acid-catalyzed hydration reagent

A

H3O+ or H2SO4 / H20

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Q

hydrohalogenation adds what

A

H + X

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Q

hydrohalogenation regiochem

A

markovnikov

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Q

hydrohalogenation intermediate

A

carbocation

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Q

hydrohalogenation stereochem

A

all

Q

hydrohalogenation reagent

A

HX

Q

oxymercuration-demercuration adds what

A

H+OH

Q

oxy-dem regiochem

A

markovnikov

Q

oxy-dem intermediate

A

bridged mercurinium ion, radical

Q

oxy-dem reagent

A

1)Hg(OAc)2, H20 / 2) NaBH4

Q

oxy-dem stereochem

A

flip product upside down if chiral, all bc of radican

Q

hydroboration oxidation adds what

A

H+OH

Q

hydroboration oxidation regiochem

A

anti-Markovnikov

Q

hydroboration oxidation sterochem

A

syn addition

Q

hydroboration oxidation intermediate

A

BOOH complex

Q

hydroboration oxidation reagent

A

1) BH3 THF / 2) H202, NaOH

Q

Catalytic hydrogenation adds what

A

H+H

Q

catalytic hydrogenation stereochem

A

syn addition

Q

catalytic hydrogenation reagent

A

H2/Pdc, Pt, Ni, or Rh

Q

halogenation adds what

A

X + X

Q

halogenation stereochem

A

anti addition and flip products upside down

Q

halogenation intermediate

A

bromonium 3 membered ring

Q

Syn dihydroxylation adds what

A

OH + OH

Q

syn dihydroxylation stereochem

A

syn addition

Q

syn dihydroxylation intermediate

A

cyclic osmate ester

Q

syn dihydroxylation reagent

A

1) OsO4/ 2) NMO or NaHSO4, H20
or
KMnO4/cold

Q

ozonolysis does what

A

cleave double bond to produce ketones and aldehyde or carboxylic acids

Q

ozonolysis reductive

A

Zn or DMS reagent, aldehyde, keeps H

Q

ozonolysis oxidative

A

H2O2 reagent, if H is there add O

Q

ozonolysis intermediate

A

molozonide and ozonide

Q

Hydrohalogenation w/ ROOR adds what

A

H + X

Q

hydrohalogenation w/ ROOR regiochem

A

anti-Markovnikov

Q

hydrohalogenation w/ ROOR intermediate

A

radical

Q

hydrohalogenation w/ ROOR reagent

A

HX/ROOR