TAILIEUCHUNG - Carboxyl Derivatives

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups. The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex. Other organic carbonyls are urea and the carbamates, the derivatives of acyl chlorides chloroformates and phosgene, carbonate esters, thioesters, lactones, lactams, hydroxamates, and isocyanates. Examples of inorganic carbonyl compounds are carbon dioxide and carbonyl sulfide | replacement of -OH in a sulfonic acid by -Cl gives a sulfonyl chloride 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 Cyclic anhydrides are named from the dicarboxylic acids from which they are derived The functional group of an ester is an acyl group bonded to -OR or -OAr name the alkyl or aryl group bonded to oxygen followed by the name of the acid change the suffix -ic acid to -ate Cyclic esters are called lactones name the parent carboxylic acid, drop the suffix -ic acid, and add -olactone The functional group of an amide is an acyl group bonded to a nitrogen atom IUPAC: drop -oic acid from the name of the parent acid and add -amide if the amide nitrogen is bonded to an alkyl or aryl group, name the group and show its location on nitrogen by N- Cyclic amides are called lactams Name the parent carboxylic acid, drop the suffix -ic acid and add -lactam The functional group of a nitrile is a cyano group IUPAC: name as an alkanenitrile Common: drop the -ic acid and add -onitrile Amides are comparable in acidity to alcohols water-insoluble amides do not react with NaOH or other alkali metal hydroxides to form water soluble salts Sulfonamides and imides are more acidic than amides Imides are more acidic than amides because 1. the electron-withdrawing inductive of the two adjacent C=O groups weakens the N-H bond, and 2. the imide anion is stabilized by resonance delocalization of the negative charge imides such as phthalimide readily dissolve in aqueous NaOH as water-soluble salts 1H-NMR H on the -carbon to a C=O group are slightly deshielded and come into resonance at H on the carbon of the ester oxygen are more strongly deshielded and come into resonance at 13C-NMR the carbonyl carbons of esters show characteristic resonance at 160-180 Nucleophilic

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