8303119-039-Reacts-Benzene

8303119-039-Reacts-Benzene - Chem Factsheet September 2002...

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Reactions of Benzene and its Compounds C hem F actsheet September 2002 Number 39 1 To succeed in this topic you need to: Have a good understanding of AS-level Organic Chemistry (Factsheets 15, 16,17, and 27); Be confident in using organic nomenclature and structural formulae. After working through this Factsheet you will: Be able to explain the structure of benzene; Know the names and structures of common substituent products of benzene; Know the necessary reactions of benzene and its compounds. Benzene, C 6 H 6 , is an aromatic hydrocarbon, or an arene . When the formula was first found, the structure proposed initially was: Derivatives of benzene Derivatives of benzene are formed by substitution reactions which will be electrophilic in nature due to the high concentration of electrons in the delocalised system of benzene. H H H H H H This structure would have resulted in bonds having different lengths; double bonds are shorter than single bonds, due to the greater attractive forces. If this had been the correct structure, two equivalent forms would have existed: However, where equivalent bond structures can be written for a compound neither exist. Instead, all bond lengths will be equal as the available electrons are shared equally amongst the atoms involved. The benzene ring consists of 6 C-C single bonds and the remaining electrons exist in a delocalised system . The structure of benzene is often written: In this representation the H atoms need not be shown. The C-C bonds are somewhere between single and double bonds, as illustrated by the following bond length data: C-C single bond length in cyclohexene = 0.15 nm C=C double bond length in cyclohexene = 0.13 nm But C-C bond length in benzene = 0.14 nm Benzene is a clear colourless liquid at room temperature and pressure. It is relatively unreactive due to the strong bonding within its structure Benzene used to be used as a non-polar organic solvent, but this is no longer the case due to its carcenogenic (cancer causing) properties. H
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8303119-039-Reacts-Benzene - Chem Factsheet September 2002...

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