lecture 18.1

lecture 18.1 - Organic Organic H BrownWilliam H...

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Unformatted text preview: 18-18-11Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson18-18-22FunctionalFunctionalDerivatives ofDerivatives ofCarboxylic AcidsCarboxylic Acids18-18-33Carboxyl DerivativesCarboxyl Derivatives◆In this chapter, we study five classes of organic compounds•under the structural formula of each is a drawing to help you see its relationship to the carboxyl groupH-NH2H-ClH-OR'RC-OHOH-OCR'ORC=NHO HRC-OHORC-OHORC-OHO-H2O-H2O-H2O-H2O-H2ORC NRCNH2ORCClORCOR'ORCOCR'O OThe enol ofan amideAn acidchlorideAn esterAn acidanhydrideAn amideA nitrile18-18-44Structure: Acid ChloridesStructure: Acid Chlorides◆The functional group of an acid halide is an acyl group bonded to a halogen•the most common are the acid chlorides•to name, change the suffix -ic acid-ic acid to -yl halide-yl halideCH3CClOORC-ClOClOClOBenzoyl chlorideEthanoyl chloride(Acetyl chloride)An acyl groupHexanedioyl chloride(Adipoyl chloride)18-18-55Sulfonyl ChloridesSulfonyl Chlorides•replacement of -OH in a sulfonic acid by -Cl gives a sulfonyl chlorideSOHH3COOCH3SOHOOSClH3COOCH3SClOOMethanesulfonicacid p-Toluenesulfonic acidMethanesulfonyl chloride(Mesyl chloride, MsCl) p-Toluenesulfonyl chloride (Tosyl chloride, TsCl)18-18-66Acid AnhydridesAcid Anhydrides◆The functional group of an acid anhydride is two acyl groups bonded to an oxygen atom•the anhydride may be symmetrical (two identical acyl groups) or mixed (two different acyl groups)•to name, replace acidacid...
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This note was uploaded on 03/30/2008 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

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lecture 18.1 - Organic Organic H BrownWilliam H...

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