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An Introduction to the Chemistry of Benzenoid Compounds - download pdf or read online

By Muriel Tomlinson

ISBN-10: 0080156592

ISBN-13: 9780080156590

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3 100 2 37 27 X 6 , . = 60-0. fp = — x 100 1 , DISUBSTITUTION IN BENZENOID COMPOUNDS 33 Because by definition the partial rate factor of benzene is one, it is clear that even the m-position of toluene is slightly more reactive than any position in benzene. The nitration of ethyl benzoate in acetic anhydride at 18° provides an example where all the positions are deactivated compared to benzene. The relative reactivity of the ester is found to be 0 · 00367 : 1 . The observed proportions and the calculated partial rate factors are 24% ortho which gives fa= 0-0026, 72% meta which gives fm= 0-0079, 4% para which gives fp= 0-0009.

The nitration of ethyl benzoate in acetic anhydride at 18° provides an example where all the positions are deactivated compared to benzene. The relative reactivity of the ester is found to be 0 · 00367 : 1 . The observed proportions and the calculated partial rate factors are 24% ortho which gives fa= 0-0026, 72% meta which gives fm= 0-0079, 4% para which gives fp= 0-0009. -brominations are Phenol fp Acetanilide /ρ Dimethylaniline/ P These, then, are some of the facts aromatic substitution must explain.

Reduction of (5) with sodium dithionite produces dibenzene chromium (6) which (5) (6) THE ADDITION REACTIONS OF THE BENZENE NUCLEUS 55 is a surprisingly stable brown solid. It is soluble in benzene, can be sublimed in vacuo, and decomposes at about 300°. Ozonisation, reduction, and addition of halogens are examples of the second type of addition. Although the benzene ring is very stable to ordinary oxidising agents, ozone reacts slowly with benzene to form a triozonide, and boron trifluoride will catalyse the reaction.

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An Introduction to the Chemistry of Benzenoid Compounds by Muriel Tomlinson


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