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Read e-book online Aromatic Chemistry. Organic Chemistry for General Degree PDF

By P. W. G. Smith

ISBN-10: 008012948X

ISBN-13: 9780080129488

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Substitution in Disubstituted Benzenes In the case of further substitution in a disubstituted benzene, the most likely orientation of the incoming group may often be predicted with some degree of confidence by considering the result of combining the individual orienting effects of the substituents already present. The following cases are illustrative and other examples will be found in the subsequent chapters. If the orienting effects reinforce one another the preferred position (or positions) of attack may readily be deduced, as in the case of the nitration of w-dinitrobenzene (XXII) or of p-nitrotoluene (XXIII).

G. the fluoroborate, p. g. 1 Θ Ν ξ N}BK4 NO, NO, NaNO, HQ ^ r 1 NaBF4 NO, NO, ( 1 1 NO2 NaNO, Cu 1 Secondly, primary amines may be oxidised to nitro compounds by reaction with peracids. Permonosulphuric acid (Caro's acid), peracetic acid, or acidified aqueous hydrogen peroxide may be used. g. SOg NO2 HNO3 o,N General Reactions As the aromatic mononitro compounds have no a-hydrogen atoms they resemble tertiary nitroparaffins in being indifferent to cold aqueous alkali. It should be noted however that many polynitro compounds form coloured complexes with alcoholic potassium hydroxide and give characteristic colours when shaken in acetone with aqueous alkali (Janowsky's reaction).

Nucleophilic replacements. g. in chlorobenzene) are illustrated by the following examples. ) ^J"'? ) ^^"ff" C^Hs-CN+KCl C6H5OH -f NaCl The preferred large-scale procedure for the preparation of phenol from chlorobenzene employs superheated steam at 475" in the presence of suitable catalysts. Example (b) represents a commercial route to aniline but the yield of benzonitrile in example (c) is poor. g. —NO2) are situated ortho or para (but not meta) to the displaced g r o u p ; for example, the hydrolysis of /7-chloronitrobenzene with aqueous alkali proceeds relatively readily.

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Aromatic Chemistry. Organic Chemistry for General Degree Students by P. W. G. Smith


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