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z-CH. 7 Organic reaction
CHM2210 Dr. Dixon Summer 09
16
Organic Chemistry
Undergraduate 2
07/06/2009

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Term
Addition of HX
Definition
(R,R)C=C(R,R)--HX/Ether-->(R,R)H-C-C-X(R,R)

H to less substituted C
Markovnikov regiochemistry occurs
Term
Addition of Halogens
Definition
(R,R)C=C(R,R)--X2/CH2Cl2-->(R,R)X-C-C-X(R,R)

Br2, Cl2
Anti-addition through halonium ion intermediate
Term
Halohydrin Formation
Definition
(R,R)C=C(R,R)--X2/H2O-->(R,R)X-C-C-OH(R,R)

Markovnikov regiochemistry and anti stereochemistry occur
Term
Addition of Water by Oxymercuration
Definition
(R,R)C=C(R,R)--1.Hg(OAc)2/2.NaBH4-->(R,R)H-C-C-X(R,R)

Markovnikov regiochemistry occurs
Term
Addition of Water by Hydroboration/Oxidation
Definition
(R,R)C=C(R,R)--1.BH3, THF/2.H2O2, OH-->(R,R)H-C-C-X(R,R)


Non-Markovnikov syn addition occurs
Term
Dichlorocarbene Addition
Definition
(R,R)C=C(R,R)+CHCl3--KOH-->(R,R)H-C-C(Cl2)-C-X(R,R)
Term
Simmons-Smith Reaction
Definition
(R,R)C=C(R,R)+CH2I2--Zn(Cu)/Ether-->(R,R)H-C-C(H2)-C-X(R,R)
Term
Catalytic Hydrogenation
Definition
(R,R)C=C(R,R)--H2/Pd/C or PtO2-->(R,R)H-C-C-H(R,R)
Term
Epoxidation With a Peroxyacid
Definition
(R,R)C=C(R,R)--RCOOOH-->(R,R)-C-O-C-(R,R)
Term
Hydroxylation by Acid-Catalyzed Epoxide Hydrolysis
Definition
(R,R)-C-O-C-(R,R)--H3O+-->(R,R)HO-C-C-OH(R,R)
Term
Hydroxylation with OsO4
Definition
(R,R)-C=C-(R,R)--1.OsO4/2.NaHSO3,H2O or OsO4,NMO-->(R,R)HO-C-C-OH(R,R)
Term
Radical Polymerization
Definition
(R,H)C=C(H,H)--Radical initiator-->(R,H)-C-C-(H,H)
Term
Oxidative Cleavage of Alkenes with Ozone
Definition
(R,R)C=C(R,R)--1.O3/2.Zn/H3O+-->(R,R)C=O + O=C(R,R)
Term
Oxidative Cleavage of Alkenes with KMnO4 (non-terminal)
Definition
(R,R)C=C(R,R)--KMnO4,H3O+-->(R,R)C=O + O=C(R,R)
Term
Oxidative Cleavage of Alkenes with KMnO4 (terminal)
Definition
(R,R)C=C(R,R)--KMnO4,H3O+-->R-C(=O,OH) + CO2
Term
Cleavage of 1,2-diols
Definition
(R,R)HO-C=C-OH(R,R)--HIO4/H2O-->(R,R)C=O + O=C(R,R)
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