Chemistry - ALCOHOL & ETHER Question with Solution | TestHub

Explain Question:

The question asks to match the reactions in Column-I with their corresponding organic products listed in Column-II.

Concept:

Ether Cleavage, Nucleophilic Substitution, Diazotization, Carbocation Rearrangement

Solution:

• (A) Me–O–CH(Me)₂ + HI: This is an ether cleavage. The iodide ion attacks the smaller methyl group, leaving the isopropyl group as an alcohol. Product: (S) Isopropyl alcohol.

• (B) Ph–¹⁸O–Me + H₃O⁺: This is the acid-catalyzed hydrolysis of an aryl-alkyl ether. The O–Me bond breaks because the Ph–O bond has partial double-bond character. Products: (R) Ph¹⁸–OH and (Q) MeOH.

• (C) Me–Cl + Aq. KOH: A standard $S_N^{}2$ reaction where the hydroxide ion replaces the chloride. Product: (Q) MeOH.

• (D) CH₃–CH₂–CH₂–NH₂ + NaNO₂/HCl: This forms a primary aliphatic diazonium salt which is unstable and forms a carbocation (CH₃CH₂CH₂⁺). This rearranges to a more stable secondary carbocation, leading to (S) Isopropyl alcohol as the major product.

Matching Summary:

• A → S

• B → Q, R

• C → Q

• D → S