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17 Cards in this Set

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Add OH (markovnikov)

1)Hg (OAc)2, H2O, THF


2)NaBH4, OH -, H2O

Add OH (antimarkovnikov)

1)BH3,THF


2) H2O2, OH-

Add OH (carbonation)

H3O+/H2O

Radical bromination

HBr/tBuOOtBu


Antimarkovnikov

-Ozonolysis

1)O3, -78C, DCM


2) H2O2, OH- or (CH3)2

Formation of Epoxide

Alkene --> mCPBA/benzene, 25C

Oxidation of 2ndary alcohol (create ketone)

Options:


1) Na2Cr2O7/H2SO4


2) NaCrO4/H2SO4


3) CrO3/H2SO4, acetone


4) P.C.C./CH4,Cl2

What does the oxidation of a secondary alcohol create?

Ketone

OH 1(PRIMARY) (carboxylic acid)

Options:


1) Na2Cr2O7/H2SO4


2) 1. KMnO4, OH-/2. HCl

OH 1(primary) alcohol (aldehyde)

P.C.C./CH2Cl2

Break Epoxide

1)Et2Cu(CN)Li2/-20C, THF


2) H3O+/H2O



OR


NaOEt/EtOH (basic more substituted) -always?? Or just when break Epoxide


H2SO4/EtOH(acidic less substituted)

Ether cleavage

HBr

Cis diol

Options:


1)KMnO4/H2O,OH-,acetone


2)OsO4/NaH SO3 H2O


3) H5IO6


Trans diol

1)mCPBA


2)H3O+/H2O




KCN/DMF??

Alkyne synthesis

>2eq NaNH2/100C, -160C?, Mineral oil? Get 2 R groups



1)>5eq NaNH2/2)NH4Cl (acid) get and R and H group

Alkyne Hydration - aldehyde

1)BH(isomyl)2/2) H2O2, OH-

Alkyne Hydration - ketone

Options:


1) H3O+/H2O (slow)


2) Hg SO4/H2SO4,H2O?? (FAST)