0207-Ch18 - Chapter 18 Functional Derivatives of Carboxylic...

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Chapter 18 Functional Derivatives of Carboxylic Acids
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Carboxyl Derivatives This chapter refers to five classes of organic compounds. Under the structural formula of each is a drawing to help to see its formal relationship to the carboxyl group (= C with three bonds to hetero atom/s). Ch-18 1 H -NH 2 H -Cl H -OR' RC- OH O H -OCR' O RC=N HO H RC- O RC- O RC- 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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Ch-18 2 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 . Structure: Acid Chlorides 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) CH 3 C O = Ac Me C O C 6 H 5 C O = Bz Ph C O
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Sulfonyl Chlorides Replacement of -OH in a sulfonic acid by -Cl gives a sulfonyl chloride. Ch-18 3 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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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 . Ch-18 4 COC O O CH 3 COCCH 3 O O Benzoic anhydride Acetic anhydride C O O H C CH 3 O acetic formic anhydride
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Acid Anhydrides Cyclic anhydrides are named from the dicarboxylic acids from which they are derived: Replace acid with anhydride . Ch-18 5 Maleic anhydride O O O Phthalic anhydride Succinic anhydride O O O O O O
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Phosphoric Anhydrides A phosphoric anhydride contains two phosphoryl groups bonded to an oxygen atom. Ch-18 6 Triphosphoric acid Diphosphate ion (Pyrophosphate ion) Diphosphoric acid (Pyrophosphoric acid) HO-P-O-P-OH - O-P-O-P-O - HO-P-O-P-O-P-OH - O-P-O-P-O-P-O - Triphosphate ion OH O O O - O O - O O - O O - O O - O O - O O - O - O O
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Esters The functional group of an ester is an acyl group bonded to an alkoxy group (-OR) or aryloxy group (-OAr). Name the alkyl or aryl group bonded to oxygen followed by the name of the acid by changing the suffix -ic acid to -ate . Ch-18 7 O O EtO O OEt O O O Ethyl ethanoate (Ethyl acetate) Diethyl butanedioate (Diethyl succinate) Isopropyl benzoate
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Lactones Lactone : A cyclic ester. Name the parent carboxylic acid, drop the suffix -ic acid and add -lactone (for IUPAC name of acid) or -olactone (for common name of acid). Position of C-atom that connects to the O-atom in the ring: Number , when IUPAC name of acid is used; Greek letter , when common name of acid is used. Ch-18 8 4-Butanolactone ( γ -Butyrolactone) 3-Butanolactone ( β -Butyrolactone) γ β α β α O O O O H 3 C 2 3 1 2 1 3 4 6-Hexanolactone ( ε -Caprolactone) ε δ γ β α O O 2 1 3 4 5 6
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Esters of Phosphoric Acid Phosphoric acid forms mono-, di-, and triesters.
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0207-Ch18 - Chapter 18 Functional Derivatives of Carboxylic...

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