Toluene (methylbenzene) reacts with reagent A to give compound 9. Compound 9 is then treated with reagent B to give the product(s) as shown in Scheme 1. i. What is

the electrophilic species in the first reaction? Show how the electrophile is generated from reagent A. Using curly arrows, draw a mechanism showing the reaction of toluene with this electrophile. i. Draw the possible product(s) (10) that may be formed when compound 9 reactswith reagent B. ii. Suggest, with reasons, which of these (10) is likely to be the major product from this reaction. c. (2 marks) Would you expect compound 9 to react more readily or less readily with electrophiles than toluene? Explain how you arrived at your answer. d. (8 marks) Compound 9, when treated with reagent C, is converted to compound 11,which is converted to toluene-diazonium chloride (12) after treatment with reagent D.The reaction of 12 with compound 13 gives a dye (14) as shown in Scheme 1. Write out reagents C and D and draw chemical structures of compounds 11 and 13.