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JEE Advanced2024Paper 1CHEM-III
Q.

In the following reaction sequence, the major product P is formed.

Glycerol reacts completely with excess P in the presence of an acid catalyst to form Q. Reaction of Q with excess NaOH followed by the treatment with CaCl yields Ca-soap R, quantitatively. Starting with one mole of Q, the amount of R produced in gram is ______.

[Given, atomic weight: H = 1, C = 12, N = 14, O = 16, Na = 23, Cl = 35, Ca = 40]

Solution

Step 1: oxymercuration-demercuration of the terminal alkyne with Hg/HO gives the methyl ketone .

Step 2: Clemmensen reduction (Zn-Hg/HCl) reduces the new ketone to -CH- giving .

Step 3: acid hydrolysis of the ester yields the C saturated fatty acid: P = (stearic acid, molar mass = g/mol).

Glycerol + 3 P (acid catalyst) gives the triglyceride Q (glyceryl tristearate). One mole of Q contains 3 moles of stearate units.

Q + excess NaOH (saponification) gives 3 moles of sodium stearate + 1 mole of glycerol. Treating sodium stearate with CaCl converts every 2 moles of to 1 mole of calcium stearate .

From 3 moles of sodium stearate (out of 1 mole of Q), we get moles of R.

Molar mass of R: g/mol (stearate anion ).

Mass of R = g.

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