Chapter 11: Problem 214
Draw the principal resonance forms of the nitronium ion.
Chapter 11: Problem 214
Draw the principal resonance forms of the nitronium ion.
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Get started for freeHow 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?
Is \(\mathrm{BH}_{3}\) a nucleophile or an electrophile? Explain.
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.
Give structures and names of the principal organic products expected from the monosulfonation of: (a) cyclohexylbenzene (d) m-nitrophenol (b) benzenesulfonic acid (e) o-fluoroanisole (c) salicylaldehyde (f) o-nitroacetanilide \(\left(\mathrm{O}-\mathrm{HOC}_{6} \mathrm{H}_{4} \mathrm{CHO}\right) \quad\left(\mathrm{o}-\mathrm{O}_{2} \mathrm{NC}_{6} \mathrm{H}_{4} \mathrm{NHCOCH}_{3}\right)\) (g) o-xylene
Even though \(1,3,5-\) trinitrobenzene (TNB) has more shattering power (more brisance) and is no more dangerous to handle, \(2,4,6-\) trinitrotoluene (TNT) has always been the high explosive in more general use. Can you suggest a reason (connected with manufacture) for the popularity of TNT? (Benzene and toluene are both readily available materials; for many years benzene was cheaper.)
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