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Universities » Siena College (SIENA) » CHEM - Chemistry and Biochemistr.. » 220 - Organic Chem II Lect » Flash Cards

Chapter 18 - Flashcards

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Class:CHEM 220 - Organic Chem II Lect
Subject:Chemistry and Biochemistry
University:Siena College
Term:Spring 2010
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Alkoxymercuration/demercuration alkene + 1.ROH (CF3CO2)2HG 2. NaBH4
Williamson Ether Synthesis The Williamson ether synthesis is an organic reaction, forming an ether from a organohalide and an alcohol. RO- + R'Ch2X---------ROCH2R'
Clevage by HBr or HI R-O-R' -----(HX/H2O)-----RX R'OH
Claisen Rearrangement The Claisen rearrangement (not to be confused with the Claisen condensation) is a powerful carbon-carbon bond-forming chemical reaction discovered by Rainer Ludwig Claisen. Ph-o-ch2chch (heat)
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Acid Catalyzed Epoxide opening trans diol, trans alcohol and halide
Epoxide formation Alkene + peroxy acid
Base-Catalyzed Epoxide opening result is trans alcohol and alkoxy group. RO-, ROH RMgX+ epoxide (1 ether, 2 H3O+)
Thiol In organic chemistry, a thiol is a compound that contains the functional group composed of a sulfur-hydrogen bond (-SH). RCH2Br (1.(H2N)2C=S/1.H2O, NaOH)----RCH2SH
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Oxidation of Thiol to Disulfide 2 RSH (I2, H2O) RS-SR
Sulfides A sulfide (sulphide in British English) is an anion of sulfur in its lowest oxidation number of 2. Sulfide is also a slightly archaic term for thioethers, a common type of organosulfur compound that are well known for their bad odors. RS- + R'CH2Br----RSCH2R'
Oxidation of sulfides to sulfoxides and sulfones R-S-R (H2O2) to get sulfone use a peroxy acid on the sulfoxide.
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 Alkoxymercuration/demercurationalkene + 1.ROH (CF3CO2)2HG
2. NaBH4
 Williamson Ether SynthesisThe Williamson ether synthesis is an organic reaction, forming an ether from a organohalide and an alcohol.

RO- + R'Ch2X---------ROCH2R'
 Clevage by HBr or HIR-O-R' -----(HX/H2O)-----RX R'OH
 Claisen RearrangementThe Claisen rearrangement (not to be confused with the Claisen condensation) is a powerful carbon-carbon bond-forming chemical reaction discovered by Rainer Ludwig Claisen.

Ph-o-ch2chch (heat)
 Acid Catalyzed Epoxide openingtrans diol, trans alcohol and halide
 Epoxide formationAlkene + peroxy acid
 Base-Catalyzed Epoxide openingresult is trans alcohol and alkoxy group.

RO-, ROH

RMgX+ epoxide (1 ether, 2 H3O+)
 ThiolIn organic chemistry, a thiol is a compound that contains the functional group composed of a sulfur-hydrogen bond (-SH).

RCH2Br (1.(H2N)2C=S/1.H2O, NaOH)----RCH2SH
 Oxidation of Thiol to Disulfide2 RSH (I2, H2O) RS-SR
 SulfidesA sulfide (sulphide in British English) is an anion of sulfur in its lowest oxidation number of 2. Sulfide is also a slightly archaic term for thioethers, a common type of organosulfur compound that are well known for their bad odors.

RS- + R'CH2Br----RSCH2R'
 Oxidation of sulfides to sulfoxides and sulfonesR-S-R (H2O2)

to get sulfone use a peroxy acid on the sulfoxide.
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