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THE CHEMISTRY OF ARENES A guide for A level students KNOCKHARDY PUBLISHING INTRODUCTION This Powerpoint show is one of several produced to help students understand selected topics at AS and A2 level Chemistry.
It is based on the requirements of the AQA and OCR specifications but is suitable for other examination boards. Individual students may use the material at home for revision purposes or it may be used for classroom teaching if an interactive white board is available. Accompanying notes on this, and the full range of AS and A2 topics, are available from the KNOCKHARDY SCIENCE WEBSITE at... www.argonet.co.uk/users/hoptonj/sci.htm Navigation is achieved by... either clicking on the grey arrows at the foot of each page or using the left and right arrow keys on the keyboard ARENES KNOCKHARDY PUBLISHING CONTENTS Prior knowledge Structure of benzene Thermodynamic stability Delocalisation Electrophilic substitution Nitration Chlorination Friedel-Crafts reactions Further substitution ARENES Before you start it would be helpful to… know the functional groups found in organic chemistry know the arrangement of bonds around carbon atoms recall and explain electrophilic addition reactions of alkenes ARENES STRUCTURE OF BENZENE Primary analysis revealed benzene had... an empirical formula of CH and a molecular mass of 78 and a formula of C6H6 STRUCTURE OF BENZENE Primary analysis revealed benzene had... an empirical formula of CH and a molecular mass of 78 a formula of C6H6 Kekulé suggested that benzene was... PLANAR CYCLIC and HAD ALTERNATING DOUBLE AND SINGLE BONDS STRUCTURE OF BENZENE HOWEVER... • it did not readily undergo electrophilic addition - no true C=C bond • only one 1,2 disubstituted product existed • all six C—C bond lengths were similar; C=C bonds are shorter than C-C • the ring was thermodynamically more stable than expected STRUCTURE OF BENZENE HOWEVER... • it did not readily undergo electrophilic addition - no true C=C bond • only one 1,2 disubstituted product existed • all six C—C bond lengths were similar; C=C bonds are shorter than C-C • the ring was thermodynamically more stable than expected To explain the above, it was suggested that the structure oscillated between the two Kekulé forms but was represented by neither of them.
It was a RESONANCE HYBRID.
THERMODYNAMIC EVIDENCE FOR STABILITY When unsaturated hydrocarbons are reduced to the corresponding saturated compound, energy is released.
The amount of heat liberated per mole (enthalpy of hydrogenation) can be measured.
THERMODYNAMIC EVIDENCE FOR STABILITY 2 3 - 120 kJ mol-1 When cyclohexene (one C=C bond) is reduced to cyclohexane, 120kJ of energy is released pe
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