JEE Main levelNumerical answerDifficulty 2 of 3o1130
Methyl 4-(4-hydroxyphenyl)-4-oxobutanoate, p-HO−CX6HX4−CO−CHX2CHX2−COOCHX3, is treated with a large excess of CHX3MgBr in dry ether. Counting convention: each acidic O-H (alcohol, phenol or carboxylic acid) consumes 1 mole of CHX3MgBr; each aldehyde or ketone C=O consumes 1 mole; each ester consumes 2 moles (the ketone formed after loss of alkoxide is attacked as well); deprotonation of alpha C-H is ignored. How many moles of CHX3MgBr are consumed per mole of the substrate? (Give the answer as an integer.)
Numerical answer type, tolerance 0.5.
Answer: 4
The phenol O-H consumes 1 mole (giving CHX4), the aryl ketone C=O consumes 1 mole, and the methyl ester consumes 2 moles. Total = 1 + 1 + 2 = 4 moles.