JEE Advanced levelSingle correct optionDifficulty 3 of 3o1145
Acetone is subjected to (i) NaCN, dilute HX2SOX4; (ii) HX3OX+, heat (complete hydrolysis); (iii) concentrated HX2SOX4, heat. The final product is
A2-methylprop-2-enoic acid (methacrylic acid)
B2-methylpropanoic acid
C2-hydroxy-2-methylpropanamide
D3-hydroxy-2-methylpropanoic acid
Answer: A
Step (i) gives acetone cyanohydrin (CHX3)X2C(OH)−CN. Step (ii) hydrolyses −CN to −COOH giving (CHX3)X2C(OH)−COOH. Step (iii) dehydrates the tertiary alcohol to the alkene CHX2=C(CHX3)−COOH.