Consider the reaction of a carboxylic acid, an alcohol, and 2-chloro-N-methylpyridininium iodide (D, see below) in the presence of base. Based on your knowledge of pyridinium compounds, suggest a mechanism and product for this reaction.You do not need to draw resonance structures. Suggest a synthetic route from 2-methylaniline to 2-amino-3,8-dimethylquinoline.Include all necessary intermediates and reagents. Also include the name of any named reactions you chose. A student planned a Friedel-Crafts reaction involving thiophene and maleic anhydride to give product X. The reaction required vigorous conditions including high pressure and it gave a product Y. Compound Y showed no evidence of aromaticity and contained a succinic anhydride fragment (shown). Suggest a structure for Y and use 'curly' arrows to show the mechanism for its formation.

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