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NEET CHEMISTRYHaloalkanes and HaloarenesMedium

Question

An organic compound A (C4H9Cl\text{C}_4\text{H}_9\text{Cl}) in reaction with Na\text{Na}/diethyl ether gives a hydrocarbon which on monochlorination gives only one chloro derivative. A is:

A

t-butyl chloride

B

sec-butyl chloride

C

Isobutyl chloride

D

n-butyl chloride

Step-by-Step Solution

The reaction of an alkyl halide with sodium metal in dry ether to form a higher alkane is known as the Wurtz reaction . When tert-butyl chloride (C4H9Cl\text{C}_4\text{H}_9\text{Cl}) reacts with Na\text{Na} in diethyl ether, it theoretically yields 2,2,3,3-tetramethylbutane: 2(CH3)3C-Cl+2Nadry ether(CH3)3C-C(CH3)3+2NaCl2(\text{CH}_3)_3\text{C-Cl} + 2\text{Na} \xrightarrow{\text{dry ether}} (\text{CH}_3)_3\text{C-C}(\text{CH}_3)_3 + 2\text{NaCl} The resulting hydrocarbon, 2,2,3,3-tetramethylbutane, is highly symmetrical. All 18 of its hydrogen atoms are equivalent (all are primary hydrogens belonging to the six methyl groups attached to equivalent quaternary carbons). Because all the hydrogen atoms are identical, its free radical monochlorination will result in the replacement of any one of these hydrogens, yielding only a single monochloro derivative (1-chloro-2,2,3,3-tetramethylbutane). The other butyl chlorides yield hydrocarbons with multiple non-equivalent hydrogen atoms, which would produce a mixture of several monochloro derivatives.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Haloalkanes and Haloarenes. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYHaloalkanes and Haloarenesorganiccompoundtextctexthtextclreactiontextnadiethyl

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