Question

Reaction of iso-propylbenzene with O₂ followed by the treatment with H₃O⁺ forms phenol and a by-product P. Reaction of P with 3 equivalents of Cl₂ gives compound Q. Treatment of Q with Ca(OH)₂ produces compound R and calcium salt S.
The correct statement(s) regarding P, Q, R and S is(are)

• A. Reaction of P with R in the presence of KOH followed by acidification gives
  
• B. Reaction of R with O₂ in the presence of light gives phosgene gas
• C. Q reacts with aqueous NaOH to produce Cl₃CCH₂OH and Cl₃CCOONa
• D. S on heating gives P

Answer 1

The Correct Option is A, B, D

Step 1: Understanding the Formation of P 

The oxidation of iso-propylbenzene (cumene) in the presence of \( O_2 \) and acidic hydrolysis leads to the formation of phenol and acetone (P).

Step 2: Formation of Q

Reaction of P (acetone) with three equivalents of chlorine (\( Cl_2 \)) leads to the formation of trichloroacetone (Q).

Step 3: Formation of R and S

Treatment of Q with \( Ca(OH)_2 \) results in hydrolysis to form:

• Chloroform (R)
• Calcium acetate (S)

Step 4: Verifying the Statements

• (A) P reacts with R (chloroform) in the presence of \( KOH \), leading to a condensation reaction forming the given compound.
• (B) R (chloroform) undergoes photochemical oxidation with \( O_2 \) to produce phosgene gas.
• (C) Q does not react with \( NaOH \) to form the given products.
• (D) S (calcium acetate) upon heating produces acetone (P).

Conclusion:

The statements have been analyzed, and the correct ones are identified.

Answer 2

To solve the problem, we need to analyze the reaction sequence starting from iso-propylbenzene and verify the statements about compounds P, Q, R, and S.

1. Reaction of iso-propylbenzene with O₂ and H₃O⁺:
Iso-propylbenzene undergoes oxidation to form phenol and a by-product P (which is likely trichloromethylphenol or related compound).

2. Reaction of P with 3 equivalents of Cl₂ to give Q:
P reacts with chlorine to form compound Q containing trichloromethyl groups (CCl₃).

3. Treatment of Q with Ca(OH)₂ produces R and calcium salt S:
This reaction yields compound R, which has chloroform-like structure, and S, the calcium salt of a carboxylic acid.

4. Verifying the given statements:

(A) Reaction of P with R in the presence of KOH followed by acidification gives the compound shown with a CCl₃ and hydroxyl groups:
This is correct as it corresponds to the haloform reaction forming trichloromethyl derivatives.

(B) Reaction of R with O₂ in presence of light gives phosgene gas (COCl₂):
This is correct because R contains chloroform-like structure that can yield phosgene under these conditions.

(C) Q reacts with aqueous NaOH to produce Cl₃CCH₂OH and Cl₃CCOO^-Na⁺:
This is incorrect as Q is expected to form other products, not the ones stated.

(D) Heating S gives back P:
This is correct as the calcium salt S decomposes upon heating to give P.

Final Answer:
Statements (A), (B), and (D) are correct.