Chapter 17: Q15P (page 868)
Propose products (if any) and mechanisms for the following AICI3-catalyzed reactions:
猞 chlorocyclohexane with benzene
猞 methyl chloride with anisole
猞 3-chloro-2,2-dimethylbutane with isopropylbenzene
Short Answer



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Chapter 17: Q15P (page 868)
Propose products (if any) and mechanisms for the following AICI3-catalyzed reactions:
猞 chlorocyclohexane with benzene
猞 methyl chloride with anisole
猞 3-chloro-2,2-dimethylbutane with isopropylbenzene



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Which reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.
Reagents Desired Product
(a) benzene + n-butyl bromide n-butylbenzene
(b) ethylbenzene + tert-butyl chloride p-ethyl-tert-butylbenzene
(c) bromobenzene + ethyl chloride p-bromoethylbenzene
(d) benzamide (PhCONH3) + CH3 CH2 CI p-ethylbenzamide
(e) toluene + HNO3, H2SO4 , heat 2,4,6-trinitrotoluene (TNT)
What products would you expect from the following reactions?

Starting with benzene and any other reagents you need, show how you would synthesize the compound shown here. (Hint: Consider a Pd-catalyzed coupling for the final step).

Predict the products formed when m-cresol (m-methylphenol) reacts with
(a) NaOH and then ethyl bromide
(b) CH3 acetyl chloride, CH3COCI
(c) bromine in CCI4 in the dark
(d) excess bromine in CCI4 in the light
(e) sodium dichromate in H2SO4
(f) two equivalents of tert-butyl chloride and AICI3
What organocuprate reagent would you use for the following substitutions?

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