Consider the following sequence of reactions to give the major product (X) [figure] P g of the major product (X) formed is reacted with NaHCO3 solution to liberate a gas which occupied 11.2 dm3 at STP. P = g. (Given molar mass in g mol-1 H : 1, C : 12, O : 16, Cl : 35.5)
Answer
78
Solution
Friedel–Crafts methylation gives toluene; -CH3 is o/p-directing, so chlorination gives mainly p-chlorotoluene; K2Cr2O7/H2SO4 oxidises -CH3 to –COOH:
[figure]
X = 4-chlorobenzoic acid, ClC6H4COOH (C7H5ClO2)
Molar mass = 7(12) + 5(1) + 35.5 + 2(16) = 156.5 g mol-1
ClC6H4COOH + NaHCO3 ClC6H4COONa + H2O + CO2
Moles of CO2 = 11.222.4 = 0.5 mol = moles of X
⇒ P = 0.5 × 156.5 = 78.25 g ≈ 78 g
Answer: 78