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COMEDK · Chemistry · 26. Alcohols Phenols and Ethers

Compounds \(\mathrm{A}\) and \(\mathrm{B}\), having the same molecular formula \((\mathrm{C}_4 \mathrm{H}_8 \mathrm{O})\), react separately with \(\mathrm{CH}_3 \mathrm{MgBr}\), followed by reaction with dil. \(\mathrm{HCl}\) to form compounds \(\mathrm{X}\) and \(\mathrm{Y}\) respectively. Compound \(\mathrm{Y}\) undergoes acidic dehydration in presence of Conc. \(\mathrm{H}_2 \mathrm{SO}_4\) much more readily than \(\mathrm{X}\). Compound \(\mathrm{Y}\) also reacts with Lucas reagent, much more readily than \(\mathrm{X}\), with appearance of turbidity. Identify \(\mathrm{X}\) and \(\mathrm{Y}\).

  1. A \(\mathrm{X}=\text { Pentan }-1-\mathrm{ol} \quad \mathrm{Y}=\text { Pentan }-2-\mathrm{ol}\)
  2. B \(\mathrm{X}=\text { Pentan-2-ol } \quad \mathrm{Y}=2 \text {-Methylbutan-2-ol }\)
  3. C \(\mathrm{X}=\text { Butan-2-ol } \quad \mathrm{Y}=\text { 2-Methylpropan-2-ol }\)
  4. D \(\mathrm{X}=\text { Pentan-1-ol } \quad \mathrm{Y}=2-\text { Methylpentan-2-ol }\)
Verified Solution

Answer & Solution

Correct Answer

(B) \(\mathrm{X}=\text { Pentan-2-ol } \quad \mathrm{Y}=2 \text {-Methylbutan-2-ol }\)

Step-by-step Solution

Detailed explanation

A and B have molecular formula \(C_4H_8O\) (carbonyl compounds). Reacting with \(CH_3MgBr\) adds one carbon, giving 5-carbon alcohols X and Y. Y undergoes dehydration and Lucas test much more readily than X \(\Rightarrow\) Y is a tertiary alcohol, X is a secondary alcohol.…