Question

Give the relative rates of reaction of isopropyl butyrate with the four reagents below to give an N-methylated amide. Give the relative rates of reaction of the four carboiylic acid derivatives below with methylamine to give an N-methyl amide. Give the relative rates of reaction of the four carboxylic acid derivatives below with excess ethanol and a trace of HCI to give an ethyl ester.

Answer 1

In sodium methylamide negative charge present on nitrogen which an electronegative atom. So, this is most reactive among all the given reagents. Na NHCH; Sodium methylamide is Tetramethylammonium chloride is the least reactive because the nitrogen atom positively charged in tetramethylammonium chloride. Chiar H3C—N—CH CH3 tetramethylammonium chloride In methylamine, nitrogen has one lone pair. Thus, it is the second most reactive among all. H3C-NH2 Methylamine Methylammonium acetate is the third most reactive among all. C H3N H3C o CH3 Methylammonium acetate Therefore,

Most reactive 2nd most reactive 3rd most reactive Least reactive The reactivity order of the acid derivates towards nucleophiles is: Acid chloride > Anhydride > Ester > Amide > Carboxylic acid The given acid derivatives are: H3c 0 CH3 Hzc OCH H3C NH2 Hzc OH acetic anhydride methyl acetate acetamide acetic acid Therefore,

Most reactive 2nd most reactive 3rd most reactive Least reactive The given acid derivatives are: بالله لليل > HEC CH3 H4C HEC CI propionyl chloride > H3C. Осн. "NH2 propionic anhydride methylpropionate propionamide Therefore, Most reactive 2nd most reactive b 3rd most reactivec Least reactive