Aromatic Chemistry by John D. Hepworth, Mike J. Waring, David R. Waring, Martyn

By John D. Hepworth, Mike J. Waring, David R. Waring, Martyn Berry, E.W. Abel, A.G. Davies, David Phillips, J.Derek Woollins, Colin Drayton

This sequence of books contains brief, single-topic or modular texts, targeting the elemental components of chemistry taught in undergraduate technology classes. each one publication presents a concise account of the fundamental rules underlying a given topic, embodying an independentlearning philosophy and together with labored examples. the single subject, one booklet method guarantees that the sequence is adaptable to chemistry classes throughout various associations.

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For example, nitration of nitrobenzene gives 88% of 1,3dinitrobenzene and only 8% and 1% of the 1,2- and 1,4-isomers, respectively. The reaction occurs at a relative rate of 6 x lo-* to that of benzene. 4. 3 Groups which Withdraw Electrons by the Inductive Effect Groups such as , CF,, and , R,N+, are unable to interact with the n-system, but withdraw electrons as a result of the electronegativity of the fluorine atoms and the positively charged nitrogen, respectively. 14). The intermediates are overall destabilized by electron withdrawal, but structures 15 and 16 are particularly unfavourable because the positive charge is adjacent to the electron-deficient atom of the substituent.

13 Phenols With Formaldehyde In aqueous alkaline solution, phenol reacts with formaldehyde (methanal) at low temperatures to form a mixture of 2- and 4-hydroxybenzyl alcohols. This is another example of electrophilic attack which results in the formation of a new C-C bond. 14. These products readily lose water to form quinomethanes (methylenecyclohexadienones), which react with more phenoxide. g. Bakelite) in which the aromatic rings are linked to methylene bridges. Reaction of 2,4,5-trichlorophenol (the antiseptic TCP) with HCHO yields hexachlorophene, a widely used germicide.

I Friedel-Crafts Reaction The most important means of introducing an alkyl group into an . 1). 1 A wide range of reactants, catalysts, solvents and reaction conditions can be used, making the Friedel-Crafts reaction a very valuable and versatile process. As well as alkyl halides, alcohols and alkenes are direct sources of alkyl groups. Acyl chlorides and anhydrides are additional sources, but these involve the subsequent reduction of a carbonyl group (C=O) to a methylene (CH,) unit. A variety of catalysts, including other Lewis acids such as FeCl, and BF,, and the protic acids HF, phosphoric acid and sulfuric acid, has been used.

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