14 – Aromatic Hydrocarbons

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Presentation transcript:

14 – Aromatic Hydrocarbons Organic Chemistry 14 – Aromatic Hydrocarbons Leaving Certificate Chemistry

An aromatic compound is a compound containing a benzene ring Originally such compounds were called ‘aromatic’ as they had nice smells Benzene: C6H6

Derived from whale oil – 1825 – Michael Faraday Benzene: C6H6 Derived from whale oil – 1825 – Michael Faraday

By 1834: Molecular formula known to be C6H6 Benzene: C6H6 By 1834: Molecular formula known to be C6H6 Chemical formula suggests a highly unsaturated compound But Benzene does not decolourise bromine water OR acidified potassium permanganate Benzene undergoes substitution reactions rather than addition. Confusion

H H C C H H H H C C C C C C C C H H H H C C H H Benzene: C6H6 What is the chemical structure of benzene? H H C C H H H H C C C C C C C C H H H H C C H H

1 picometre is one trillionth of a metre Benzene: C6H6 Bond Lengths C C 154 picometres C C 134 picometres But all of the bond lengths in Benzene are of the same length of 140 picometres One very big problem 1 picometre is one trillionth of a metre

Benzene: C6H6 H C H H C C C C H H C H Benzene: C6H6 He suggested that six electrons revolve around the entire six carbon atoms and this explains why all carbon-carbon bond lengths are equal 2007 Q. 4(i) (6) C H H C C C C H H C Structure revealed by Kekule in 1865 Benzene: C6H6 H

Methylbenzene CH3 Methylbenzene is preferable for use over benzene in a laboratory as benzene is carcinogenic 2006 Q. 4 (d) (6) Used as an industrial solvent Also called toluene Methylbenzene: C7H8

Ethylbenzene C2H5 2005 Q. 4(g) (6) Ethylbenzene: C8H10

Physical properties of benzene? Physical state: Benzene, Methylbenzene and ethylbenzene are liquid at room temperature Insoluble in water Soluble in non-polar solvents such as cyclohexane