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Question #44429

Difficulty: 8/10 | 🟢 Free

The Question

An optically inactive compound $\textbf{P}$ ( $C_6H_{12}O$ ) does not decolorize $Br_2/CCl_4$ and is unreactive towards Tollens' reagent. Upon heating with dilute aqueous $H_2SO_4$ , $\textbf{P}$ yields compound $\textbf{Q}$ ( $C_6H_{14}O_2$ ). Treatment of $\textbf{Q}$ with periodic acid ( $HIO_4$ ) yields a single organic product $\textbf{R}$ . Compound $\textbf{R}$ gives a yellow precipitate when treated with $I_2$ and $NaOH$ (aq), but does not reduce Fehling's solution. What is the IUPAC name of compound $\textbf{P}$ ?

Options

A.
2,3-Epoxy-2,3-dimethylbutane
B.
1,2-Epoxy-3,3-dimethylbutane
C.
2,3-Epoxy-2-methylpentane
D.
1,2-Epoxyhexane

Check Your Answer

Correct Answer

Step-by-Step Solution

Explanation

How the Examiner Thinks

Mechanism_Trap

Don't get tricked by the process! Learn the mechanical traps used in competitive exam questions.

Concepts Behind This Question

Iodoform Reaction Requirements|Glycol Periodic Acid Cleavage

Why This Question Is Tricky

Common Mistakes

This question tests the 'Hidden Methyl Ketone Generation' trap.

Students often erroneously look for the methyl ketone moiety ( $CH_3CO-$ ) in the starting material itself, leading them to incorrectly guess a ketone precursor.

The trap requires recognizing that $HIO_4$ cleavage of a symmetrically substituted vicinal diol (generated in situ via epoxide hydrolysis) produces the reactive analyte.

The distinction between Tollens'/Fehling's and Iodoform tests isolates acetone as the only possible cleavage product that fits the criteria (single product, positive iodoform, negative Fehling's), thereby reverse-engineering the structure of the optically inactive epoxide.

Quick Facts About This Question

Question Information

Subject	Chemistry
Chapter	Alcohols, Phenols, and Ethers - Class 12
Concept	Iodoform Reaction Requirements
Difficulty	8
Cognitive Load	7
Target Solve Time	160 sec
Access	Free