By Hepworth J D (University of Central Lanc
This booklet presents an updated and finished account of fragrant chemistry. a sequence of chapters describes the synthesis and reactions of the most important useful derivatives of benzene and the extra universal polycyclic platforms. the idea that of aromaticity and the mechanism of fragrant substitution are mentioned, as is using metals within the synthesis of fragrant compounds. all through, emphasis is put on mechanisms. labored difficulties and questions are supplied to help knowing. as well as offering fabric required by means of an undergraduate learning chemistry, fragrant Chemistry can also be perfect for business chemists trying to replace their wisdom of this crucial point of chemistry. perfect for the wishes of undergraduate chemistry scholars, instructional Chemistry Texts is an incredible new sequence inclusive of brief, unmarried subject or modular texts focusing on the basic components of chemistry taught in undergraduate technology classes. every one e-book offers a concise account of the fundamental ideas underlying a given topic, embodying an independent-learning philosophy and together with labored examples.
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Extra info for Aromatic Chemistry (Tutorial Chemistry Texts)
The Reimer-Tiemann Reaction Treatment of a phenol with chloroform (trichloromethane) in the presence of hydroxide ion results in the synthesis of a 2-hydroxybenzaldehyde through C-formylation. Dichlorocarbene, :CCl,, is generated by the action of base on chloroform and this highly reactive electrophile then attacks the phenoxide. 12. 12 The Kolbe-Schmidt Reaction The phenoxide ion is sufficiently nucleophilic to be attacked by carbon dioxide, providing a useful method for the introduction of a carboxylic acid group; ortho carboxylation takes place at 120-140 "C.
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. In reactions using alcohols, the favoured catalyst is BF,; HF is often used in reactions involving alkenes. The reaction can be very fast, but can be moderated by the use of an inert solvent such as nitrobenzene or carbon disulfide. The temperature at which the reaction is carried out can vary from below room temperature to about 200 "C. However, there are several drawbacks to this alkylation reaction.
Biphenyls may also be prepared using organometallic coupling (see Chapter 10). 9 Biphenyl undergoes typical electrophilic substitution reactions. The phenyl group is ortholpara directing. For example, the major product of mononitration is 4-nitrobiphenyl. Introduction of a second nitro group in the molecule occurs in the unsubstituted ring, also, mainly, in the 4'position. This might be unexpected since a nitrophenyl group is electron withdrawing, and therefore meta directing. However, irrespective of the electronic properties of the mono substituent, electrophilic substitution of a second substituent generally occurs in the 4'-position of the unsubstituted ring.