By Hepworth J D (University of Central Lanc
This ebook offers an updated and entire account of fragrant chemistry. a chain of chapters describes the synthesis and reactions of the foremost sensible derivatives of benzene and the extra universal polycyclic structures. the concept 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 assist knowing. as well as delivering fabric required by way of an undergraduate learning chemistry, fragrant Chemistry is usually excellent for business chemists looking to replace their wisdom of this significant element of chemistry. excellent for the wishes of undergraduate chemistry scholars, instructional Chemistry Texts is a big new sequence which include brief, unmarried subject or modular texts focusing on the basic components of chemistry taught in undergraduate technological know-how classes. every one booklet presents 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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Additional resources for Aromatic Chemistry (Tutorial Chemistry Texts)
1 Introduction Benzene and its simple alkyl derivatives are the building blocks of the aromatic chemical industry and are also important solvents for many reactions and processes. The simplest derivative, (methylbenzene, l),is the source of a range of nitrotoluenes and is one of the most important industrial solvents. The three isomeric dimethylbenzenes, u-, m- and p-xylene (2-4) are often used as a mixture in industrial solvents. bMe Me 2 o-xylene ( 1,2-dirnethylbenzene) 4. 2 Sources of Alkylbenzenes Traditionally, the source of benzene and toluene has been coal.
However, there are several drawbacks to this alkylation reaction. The use of longer alkyl chains than ethyl can be complicated by isomerization of the alkyl group arising from carbonium ion hydride shifts. It is therefore not uncommon for mixtures to be produced. In extreme cases, a completely different alkyl group from that of the starting material can be present in the product. A specific example is the alkylation of benzene with 1-chloropropane 39 Aromatic Chemistry 40 5 6 in the presence of aluminium chloride.
7, and hence can be considered to contribute more to the resonance hybrid. A similar situation arises with species 9 associated with attack at the 4-position and this carbocation intermediate is therefore also additionally stabilized by 10. However, no such structure can be drawn following meta attack and so the cation derived from this mode of attack is not additionally stabilized. 2. Notice that even attack at the meta position has a lower activation energy than does benzene. 2 Energy profile for electrophilic attack on methoxybenzene at the ortho, meta and para positions compared with benzene It should therefore be no surprise that the nitration of methoxybenzene is easier and faster than that of benzene and yields essentially only the 1,2- and 1,4-isomers (in almost equal amounts).
Aromatic Chemistry (Tutorial Chemistry Texts) by Hepworth J D (University of Central Lanc