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Question #44399

Difficulty: 8/10 | 🟢 Free

The Question

Consider the following reaction sequence starting from 1-chloro-1-methylcyclopentane:

$\text{1-chloro-1-methylcyclopentane} \xrightarrow[\Delta]{\ce{NaOEt / EtOH}} \text{Major Product (B)}$

$\text{(B)} \xrightarrow[2. \ce{Me2S}]{1. \ce{O3}, 195\text{ K}} \text{(C)}$

$\text{(C)} \xrightarrow[2. \ce{H3O+}]{1. \ce{I2} \text{ (excess)}, \ce{NaOH}, \Delta} \text{Yellow precipitate} + \text{(D)}$

Identify the IUPAC name of the final organic product (D).

Options

A.
Pentanedioic acid
B.
4-Formylbutanoic acid
C.
5-Oxohexanoic acid
D.
Hexanedioic acid

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

Williamson Ether Synthesis Constraints|E1/E2 Solvent and Base Effects|Steric Hindrance in SN2

Why This Question Is Tricky

Common Mistakes

This problem tests the classic 'Williamson Ether Synthesis' trap where students erroneously predict an S_N2 substitution between a tertiary halide and an alkoxide.

The hidden variable is the kinetic dominance of the E2 pathway due to steric hindrance, yielding an alkene.

Furthermore, it tests a dual-reactivity trap in the final step: students often recognize the haloform reaction for the methyl ketone but fail to account for the simultaneous oxidation of the aldehyde group by the in situ generated hypohalite ( $\ce{NaOI}$ ).

Quick Facts About This Question

Question Information

Subject	Chemistry
Chapter	Alcohols, Phenols, and Ethers - Class 12
Concept	Williamson Ether Synthesis Constraints
Difficulty	8
Cognitive Load	7
Target Solve Time	160 sec
Access	Free