Chapter 18-1 - CHEM 262 Wei You Chapter 18 Functional...

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1 CHEM 262 Wei You Chapter 18. Functional Derivatives of Carboxylic Acids (1)
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2 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 Caboxyl Derivatives
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3 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 to -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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4 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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5 Acid 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 acid of the parent acid by anhydride COC O O CH 3 COCCH 3 O O Benzoic anhydride Acetic anhydride
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6 Acid Anhydrides Cyclic anhydrides are named from the dicarboxylic acids from which they are derived M aleic anhydride O O O Phthalic anhydride Succinic anhydride O O O O O O
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