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