Chapter 22 Naming Acid hadides (Remove- ic acid and add -yl chloride) O Cl acetyl chloride or ethanoyl chloride (see also benzoyl chloride) Anhydrides Symmetrical (Remove acid and add ahydride) O O O Acetic anhydride or ethanoic anhydride Mixed Anhydride (Use both acid names, out in alphabetical order) O O O Acetic benzoic anhydride or Benzoic ethanoic anhydride Esters (The acid part becomes the root. Remove- ic acid and use –ate as the ending. The alkyl group on the oxygen becomes the first part of the name.) O Cl O O O Ethyl Acetate 2-Chloroethyl benzoate Amides (Remove- ic acid, oic acid or ylic acid and add -amide) O N N-ethyl-N-methylbenzamide Nitriles ( Use alyl name and add nitrile or remove- ic acid and add-onitrile) N C N C H C Benzonitrile 3 Acetonitile (ethanenitrile) Lactones and Lactams & other strange examples O O O NH 4-Butanolactone or γ-Butyrolactone 4-Butanolactam or γ-Butyrolactam O OEt EtO O Diethylsuccinate O O O NH O sucinnic anhydride O succinamide Reactions of acids halides. Preparation O O SOCl2 OH Cl Sample Mechanism: Acetyl chloride plus dimethyl amine. O O 2 eq. (CH3)2NH CH N 3 Cl H C 3 CH N 3 H C 3 H O : O : Cl Cl H C H C + 3 3 N N H3C H CH3 .. CH NH 3 Other acid halide reactions: O O CH 3 OMe O OH H2O Me2CuLi MeOH (pyr) (pyr) O OH O CH3 Li(tBuO)3AlH H CH3 1. 2eq MeMgBr Cl + O 2. H3O wkup Et2NH O O O (2 eq) O 2 eq NH3 O O NEt2 NH2 +NH Cl 4 Anhydrides Made from the acid chloride. Reacts in a similar way to the acid halide. A cyclic anhydride can be made from the diacid. O O OH heat O OH O O O O O H2O OH O pyridine O O O CH3OH OMe O pyridine O O O CH3NH2 (2 eq) NHCH3 O Carboxyllic acids O CH3OH O OH H2SO4 OMe O 1. NH3 O OH 2. heat NH2 O CH3NH2 O OH DCC NHCH 3 see mechanism on page 803 Fisher esterification/transesterification mechanism. H+ O CH3OH O OH H2SO4 OMe :OH2 H + O OMe H .. H H + O : O O + H O OH OH H .. + O O H C H C H 3 CH3OH 3 CH3OH H O OH O H H3C + H C O H 3 Esters O O HO OH O H H+, H O 2 OH H O 1. LiAlH 4 + + H , H2O 2. H , H2O wkup - OH , H2O O 1. CH3Li O HO 2. H+, H O O HO 2 OCH CH wkup 2 3 H+ CH3 CH3 NH3 CH3NH2 1. EtMgBr O 2. H+, H O 2 NH wkup 2 O HO Et NHCH3 Et Amides 1. LiAlH 4 O 2. H+, H O + H2N 2 O H , H O H 2 wkup OH + + NH4 H NH2 DIBAL-H 2. water OH-, H O O 2 H O O H+, H O 2 OH O O CH3 1. CH3MgBr 2. water 1. LiAlH 4 O 2. H+, H O + H2N 2 H , H O H N 2 wkup C OH H goes through amide DIBAL-H OH-, H O 2. water 2 O O O H H+, H O 2 OH O goes through amide Acid catalyzed hydrolysis of a nitrile (Compare to the base catalyzed hydrolysis on page 818.) H+ :NH3 O H2O H H3C C N + H+ O H O O H O + H C C N 3 H N H H H O H H2O + N H H O H H H N + H N H + H O + O O H O N H N H + H H H O H H H O H 2 .