Section-D: Comprehension Type
Comprehension (Carboxylic Acids and Acid-Derivatives-2)
An organic compound X(C10H12O3) is neither soluble in water nor in aqueous NaHCO3, but decolourizes solution of Br2 in CCl4 producing A(C10H12O3Br2). Upon treatment of X with ozone(O3) followed by work-up with Zn – H2O produced B(C8H8O3) and C(C2H4O2). B on refluxing with dilute, alkaline permanganate solution produced 4-hydroxy-3-methoxy benzoic acid. X on treatment with benzoyl chloride(C6H5COCl) produced D(C24H20O5) which rapidly decolourizes purple colour of aqueous permanganate solution but does not dissolve in NaOH(aq). X reacts with HI to produce E(C9H9O2I) as major product. In aqueous base, X react with CH3I to produce F(C11H14O3) which is insoluble in NaOH(aq).
Which of the following is/are chiral?