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Ch 18 - Carboxyl Derivatives O RCCl A n acid chloride-H2 O...

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Carboxyl Derivatives 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 1
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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) 2
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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) 3
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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 COC O O CH 3 COCCH 3 O O Benzoic anhydride Acetic anhydride 4
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Acid Anhydrides Cyclic anhydrides are named from the dicarboxylic acids from which they are derived Maleic anhydride O O O Phthalic anhydride Succinic anhydride O O O O O O 5
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Phosphoric Anhydrides A phosphoric anhydride contains two phosphoryl groups bonded to an oxygen atom 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 OH O O - O O - O O - O O - O O - O O - O O - O - O O 6
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Esters The functional group of an ester is an acyl group bonded to -OR (-O-alkyl) or –Oar (-O-aryl) name the alkyl or aryl group bonded to oxygen followed by the name of the acid change the suffix -ic acid to -ate O O EtO O OEt O O O Ethyl ethanoate (Ethyl acetate) Diethyl butanedioate (Diethyl succinate) Isopropyl  benzoate 7
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Esters Cyclic esters are called lactones name the parent carboxylic acid, drop the suffix -ic acid and add -olactone 4-Butanolactone -Butyrolactone) 3-Butanolactone -Butyrolactone) γ β α β α O O O O H 3 C 2 3 1 2 1 3 4 6-Hexanolactone -Caprolactone) ε δ γ β α O O 2 1 3 4 5 6 8
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Esters of Phosphoric Acid phosphoric acid forms mono-, di-, and triesters name by giving the name of the alkyl or aryl group(s) bonded to oxygen followed by the word phosphate in more complex phosphoric esters, it is common to name the organic molecule and then indicate the presence of the phosphoric ester by the word phosphate or the prefix phospho- OCH 3 CH 3 OPOH O C-H CH 2 -O-P-O - CHO HO O - O N HO H 3 C CH 2 O-P-O - O - CHO O CO - C CH 2 O P O - O - O O Dimethyl phosphate Glyceraldehyde 3-phosphate Pyridoxal phosphate Phosphoenol- pyruvate 9
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Amides The functional group of an amide is an acyl
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