Chapter 11: Problem 214
Draw the principal resonance forms of the nitronium ion.
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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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How do you account for the fact that benzene in the presence of \(\mathrm{ALCl}_{3}\) reacts: (a) with n-propyl bromide to give isopropylbenzene; (b) with isobutyl bromide to yield tert-butylbenzene; (c) with neopentyl bromide to yield tert-pentylbenzene? (d) By which of the alternative mechanisms for the Friedel-Crafts reaction are these products probably formed?
Even in dilute acidic solution, aniline, which exists mainly as the anilinium ion \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{3}{ }^{+}\right)\), undergoes o, \(\mathrm{p}\) -substitution. Account for this.
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.
Starting 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 \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{G}\).
Arrange the following in order of reactivity toward ring nitration, listing by structure the most reactive at the top, the least reactive at the bottom. (a) benzene, mesitylene \(\left[1,3,5-\mathrm{C}_{6} \mathrm{H}_{3}\left(\mathrm{CH}_{3}\right)_{3}\right]\), toluene, m-xylene, p-xylene (b) acetanilide \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHCOCH}_{3}\right)\), acetophenone \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCH}_{3}\right)\), aniline, benzene (c) \(2,4-\) dinitrochlorobenzene, 2,4 -dinitrophenol.
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