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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Certain activated benzene rings can be chlorinated by hypochlorous acid, HOCL, and this reaction is catalyzed by \(\mathrm{H}^{+}\). Can you suggest a possible function of \(\mathrm{H}^{+}\) ?
(a) The bromination of benzene is catalyzed by small amounts of iodine. Consider a possible explanation for this catalytic effect. (b) The kinetic expression for the bromination of naphthalene in glacial acetic acid involves a term that is first order in naphthalene and second order in bromine. Consider how two molecules of bromine and one of naphthalene could be involved in the rate-determining step of bromination. Suggest a reason why the kinetic expression simplifies to first order in naphthalenes and first order in bromine in 50 per cent aqueous acetic acid.
Is \(\mathrm{BH}_{3}\) a nucleophile or an electrophile? Explain.
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?
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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