Chapter 11: Problem 214
Draw the principal resonance forms of the nitronium ion.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Chapter 11: Problem 214
Draw the principal resonance forms of the nitronium ion.
These are the key concepts you need to understand to accurately answer the question.
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Get started for freeStarting with the definition of partial rate factor, derive an expression relating \(\mathrm{p}^{\mathrm{G}} \mathrm{f}\) to the rate of substitution para to \(\mathrm{G}\) in \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{G}\).
Outline all steps in the laboratory synthesis of the following compounds from benzene and/or toluene, using any needed aliphatic or inorganic reagents. Assume that a pure para isomer can be separated from an ortho, para mixture. (a) \(\mathrm{p}\) -nitrotoluene (d) p-bromobenzoic acid (b) \(\mathrm{p}\) -bromonitrobenzene (e) o-iodobenzoic acid (c) m-bromobenzenesulfonic acid (f) \(1,3,5-\) trinitrobenzene (g) 3,5 -dinitrobenzoic acid
\(2,2^{\prime}-\) Dinitrobiphenyl is to be synthesized. Outline the method of preparation from iodobenzene. No other organic reagent may be used. Any inorganic reagent may be employed.
Account for the fact that fairly reactive arenes (e.g., benzene, toluene, and ethylbenzene) are nitrated with excess nitric acid in nitromethane solution at a rate that is independent of the concentration of the arene (i.e., zeroth order). Does this mean that nitration of an equimolal mixture of benzene and toluene would necessarily give an equimolal mixture of nitrobenzene and nitrotoluenes? Why or why not?
Explain the following observations: (1) The ortho-para ratio of the products obtained by sulfonation of toluene is lower than that of nitration; (2) The ortho-para ratio of the products obtained by nitration of isopropylbenzene is lower than that of nitration of toluene.
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