2- phenylethanoic acid

Semisynthetic. In 1959, scientists at Beecham Researeh Laboratories sueceeded in isolating the penicillin nucleus, 6-aminopenicillanie aeid (6-APA Fig. 5.1 A R represents H). During the commercial production of benzylpenicillin, phenylacetic (phenylethanoic) acid (C6H5.CH2.COOH) is added to the medium in whieh the Penicillium mould is growing (see Chapter 7). This substance is a precursor of the side... 

Butan-1 -ol to butanoic acid Benzyl alcohol to phenylethanoic acid... 

Problem 16.63 Write formulas for each of the following (a) phenylacetic acid, (b) phenylethanoic acid, (c) 2-methylpropenoic acid, (d) ( )-butenedioic acid, (e) ethanedioic acid, (/) 3-methylbenzenecarboxylic acid. 

Hydroxy-2-phenylethanoic acid Propenoic acid (Z)-9-Octadecenoic acid... 

Exercise 14-10 Write a reasonable mechanism for the formation of phenylethanoic acid on heating phenylbromoethyne with potassium hydroxide in aqueous alcohol ... 

In the nuclear magnetic resonance spectra of carboxylic acids, the carboxyl proton is seen to absorb at unusually low magnetic fields. This is illustrated in Figure 18-3 by the spectra of phenylethanoic acid (C6H5CH2C02H)... 

Exercise 20-25 A first step in unravelling the mechanism of the metabolism of fatty acids was made in 1904 by F. Knoop, who found that dogs metabolized 4-phenyl-butanoic acid to phenylethanoic acid and 3-phenylpropionic acid to benzoic acid. What does this pattern of results indicate about the mechanism of degradation of fatty acids Give your reasoning. 

Exercise 26-40 Explain why p for ionization of benzoic acids is larger than p for phenylethanoic acids. Estimate a value ofp for the ionization of substituted 4-phenyl-butanoic acids. Why should we expect the value of p for alkaline hydrolysis of ethyl benzoates to be larger than for acid ionization and to have the same sign ... 

Rule-based or systematic nomenclature (e.g., International Union of Pure and Applied Chemistry [IUPAC] or CAS nomenclature) is based on a set of linguistic rules that apply to its structure. For example, the IUPAC and CAS names for mandelic acid are 2-phenyl-2-hydroxyacetic acid and benzeneacetic acid, a-hydroxy-, respectively. The number of possible systematic names is practically endless. A small, but not nearly exhaustive, set of other systematic names includes phenylglycolic acid, phe-nylhydroxyacetic acid, ( )-a-hydroxybenzeneacetic acid, ( )-a-hydroxyphenylacetic acid, ( )-2-hydroxy-2-phenylethanoic acid, ( )-Mandelic acid, (RS)-Mandelic acid, DL-Amygdalicacid,DL-Hydroxy(phenyl)aceticacid,DL-mandelicacid,paramandelic acid, a-hydroxy- a-toluic acid, a-hydroxyphenylacetic acid, a-hydroxybenzeneacetic... 

PHENYLACETATE n-BUTYL PHENYLACETATE PHENYLETHANOIC ACID BUTYL ESTER... 

Synonym phenylethanoic acid, a-toluic acid, benzeneacetic acid... 

Phenylacetic acid (phenylethanoic acid, 11), the simplest example of this type of compound, is prepared from benzyl chloride by the displacement of chloride by cyanide ion and subsequent hydrolysis to the acid (Scheme 5.13). 

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