Question

(a) 1-bromonaphthalene undergoes nucleophilic substitution reaction to give two isomeric products

i) Write a posible mechanism to explain the formation of the two products, given that the reaction involves the intermediacy of a benyne-type species. ii) In terms of orbital overlaps, briefly but clearly discuss how the ∏-bonds in this benzyne-type intermediate are formed. Explin whether or not this benzyne-type intermediate is aromatic. (b) Starting from nitrobenzene and any other benzene derivative of your choice, show by a reaction scheme how the following azo compound could be synthesised. No mechanism is required but you must show all reagents and intermediate products that are formed.

Answer 1

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