Organic Reaction Mechanisms 1988


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E) Acid halides At 25OC an equilibrium is slowly established in glacial acetic acid between acetyl chloride and acetyl fluoride in the presence of tetraethylammonium fluoride. ” Bentley’s group has published three further papers on solvolysis of benzoyl ~ h l o r i d e s . ~The ” ’ ~rates of solvolysis of 2,6-dimethyl- and 2,4,6-trimethyl-benzoyl chlorides have been reported for binary mixtures of aq. acetone, ethanol and methanol and compared with data for the solvolysisofp-methoxybenzoyl chloride, Selectivities for ester (from alcohol) and acid (from H,O) formation are almost independent of the solvent composition.

5-78%). '"'' 2 Reacrions of Acids and their Derivatives 41 Theoretical studies of the protonationlo5and hydrolysislMof methyl carbamate have been made. The ab initio MO studies included carbamic acid and methyl N-methylcarbamate also. The A 2 mechanism of acid-catalysed hydrolysis of methyl carbamate was examined by the M N D O method and found to be similar to that involved with acetamide as substrate. SiMe, (94) HO Me OR R = H, EtNHCO HO (95) R = H, EtNHCO 42 Organic Reaction Mechanisms 1988 carbamoyl phosphate, including the decomposition of the latter to cyanate and phosphate, have been determined"" and are examined later (see under Phosphoruscontaining Acids; enzymic reactions).

The possible mechanisms for the formation of these 2(5H)-furanone products are discussed. '12 At high HO- concentrations, the attack of HO- was rate-determining but at low concentrations cleavage of the uracil ring was the slow step. Il6 Crystal-structure determinations of both the amide (100) and the amine product have allowed a more precise examination of the hydrolysis which involves a tetrahedral intermediate after HO- attacks the carbonyl. The kinetics and mechanism of the acid-catalysed hydrolysis of propionamide in aq.

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