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z-Ch. 18 Ether RXNs
z-CHM2211 Dr. Elsheimer Fall 09
11
Organic Chemistry
Undergraduate 2
09/23/2009

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Cards

Term
The Williamson Ether Synthesis
Definition
R-OH -NaH/THF-> R-O- Na+ -R'Br-> R-O-R'
Term
Alkoxymercuration of Alkenes
Definition
R=R' -1.(CF3CO2)2Hg/R"OH-2.NaBH4-> R"O-R-R' markov
Term
Acidic Cleavage
Definition
R-O-R' -HX/H2O-> R-OH X-R'

Does not work with HCL
Term
Alkene to Epoxides
Definition
O2/Ag2O 300 C or m-Chloroperoxy benzoic acid/CH2Cl2
Term
Acid-Catalyzed Epoxide Opening
Definition
HX/Ether If there is a tert C on epoxide, OH goes to less substituted C
Term
Base-Catalyzed Epoxide Opening
Definition
ROH/H2O ROH deprotonates and attacks LEAST substituted C or H3O+ new OH takes MOST substituted C
Term
Thiols and Sulfides
Definition
thiol= (S) version of alcohol
SH= Mercapto
sulfide= (S) version of ether
Term
Oxidation of thiol to Disulfide
Definition
I2/Zn H+ (equilibrium)
Term
Synthesis of sulfides
Definition
RS- + R'CH2Br -> RSCH2R' + Br-
Term
Synthesis of thiols
Definition
RCH2Br -1.(H2N)2C=S/2.H2O, NaOH-> RCH2SH
Term
oxidation of sulfides to sufoxides and sulfones
Definition
R-S-R' -H2O2-> R-S=O-R' -RCO3H-> R-S=O=O-R'
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