JEE Advance - Chemistry (2011 - Paper 2 Offline - No. 20)

Match the reactions in Column I with appropriate types of steps/reactive intermediate involved in these reactions as given in Column II :

Column I Column II
(A) IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English 1 (P) Nucleophilic substitution
(B) IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English 2 (Q) Electrophilic substitution
(C) IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English 3 (R) Dehydration
(D) IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English 4 (S) Nucleophilic
(T) Carbanion

(A) $$\to$$ (R), (S), (T); (B) $$\to$$ (P); (C) $$\to$$ (R), (S); (D) $$\to$$ (Q)
(A) $$\to$$ (R), (S), (T); (B) $$\to$$ (P), (S); (C) $$\to$$ (R), (S); (D) $$\to$$ (Q), (R)
(A) $$\to$$ (R), (S), (T); (B) $$\to$$ (P), (S); (C) $$\to$$ (R); (D) $$\to$$ (Q), (R)
(A) $$\to$$ (R), (S), (T); (B) $$\to$$ (P), (S); (C) $$\to$$ (R), (S); (D) $$\to$$ (Q)

Explanation

(A)

The compound undergoes an intramolecular aldol condensation reaction in the presence of aqueous NaOH.

Steps Involved :

Abstraction of Proton :

The proton attached to the alpha carbon is abstracted, generating a carbanion.

IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 1

Nucleophilic Addition :

The carbanion attacks the electropositive carbonyl carbon, forming a cyclic intermediate.

IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 2

Dehydration :

The cyclic intermediate undergoes dehydration to yield the final product.

IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 3

Option (A) in Column I matches with (R), (S), and (T) in Column II.

(B)

Nucleophilic Addition :

The ketone reacts with methyl magnesium bromide, forming a secondary alcohol. This is a nucleophilic addition reaction.

IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 4

Nucleophilic Substitution :

The highly nucleophilic oxygen attacks the C_1 carbon of the alkyl chain from the back, displacing chlorine to form the final product.

IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 5

Option (B) in Column I matches with (P) and (S) in Column II.

(C)

Nucleophilic Addition :

The compound undergoes a nucleophilic addition reaction in the presence of $\mathrm{H}_2 \mathrm{SO}_4$.

IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 6

IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 7

Dehydration :

The molecule loses water, forming an alkene.

IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 8

Option (C) in Column I matches with (R) and (S) in Column II.

(D)

The compound reacts with sulfuric acid to form a carbocation, which undergoes electrophilic substitution.

Reaction :

IIT-JEE 2011 Paper 2 Offline Chemistry - Alcohols, Phenols and Ethers Question 10 English Explanation 9

Option (D) in Column I matches with (Q) and (R) in Column II.

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