Question

Which of the following compounds does not give iodoform test?

• A. $C{H}_{3}COC{H}_{2}COO{C}_2{H}_5$
• B. $PhC{H}_{2}COC{H}_3$
• C. $M{e}_{3}C.COC{H}_3$
• D. $C{H}_{3}COC{H}_3$

Answer 1

Answer: (A)

lodoform test is given by those compounds which contain $C{H}_{3}CO-$ group. Ethyl acetoacetate $(C{H}_{3}COC{H}_{2}COO{C}_2{H}_5)$ contains $C{H}_{3}CO-$ group but it is attached to more reactive $-C{H}_2$ group (methylene group). Therefore, on reaction with $I_2$ and $O{H}^{-},$ the iodination of $-C{H}_2$ group is rapidi than the methyl group of $C{H}_{3}CO-$ . Due to this reason ethyl acetoacetate does not give iodoform test.