lecture 18.1 - Organic Chemistry William H Brown...

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18- 18- 1 1 Organic  Organic  Chemistry Chemistry William H. Brown William H. Brown Christopher S. Foote Christopher S. Foote Brent L. Iverson Brent L. Iverson
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18- 18- 2 2 Functional Functional Derivatives of Derivatives of Carboxylic Acids Carboxylic Acids
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18- 18- 3 3 Carboxyl Derivatives Carboxyl 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 group H -NH 2 H -Cl H -OR' RC- OH O H -OCR' O RC=N HO H RC- OH O RC- OH O RC- OH O - H 2 O - H 2 O - H 2 O - H 2 O - H 2 O RC N RCNH 2 O RCCl O RCOR' O RCOCR' O O The enol of an amide An acid chloride An ester An acid anhydride An amide A nitrile
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18- 18- 4 4 Structure: Acid Chlorides Structure: 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 halide CH 3 CCl O O RC- Cl O Cl O Cl O Benzoyl chloride Ethanoyl chloride (Acetyl chloride) An acyl  group Hexanedioyl chloride (Adipoyl chloride)
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18- 18- 5 5 Sulfonyl Chlorides Sulfonyl Chlorides replacement of -OH in a sulfonic acid by -Cl gives a  sulfonyl chloride SOH H 3 C O O CH 3 SOH O O SCl H 3 C O O CH 3 SCl O O Methanesulfonic acid  p- Toluenesulfonic              acid Methanesulfonyl chloride (Mesyl chloride, MsCl)  p- Toluenesulfonyl chloride      (Tosyl chloride, TsCl)
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18- 18- 6 6 Acid Anhydrides Acid Anhydrides The functional group of an acid anhydride is two  acyl groups bonded to an oxygen atom
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