Exams › JEE Advanced › Chemistry

In which of the following pairs is the first compound more reactive than the second in an SN2 reaction?

1. Chlorobenzene; Benzyl chloride
2. Isobutyl chloride; tert-Butyl chloride
3. 2-Chlorobutane; 3-Chlorobutane
4. 1-Chloro-1-methylcyclohexane; 1-Chloro-1-methylcyclohexane

Correct answer: Isobutyl chloride; tert-Butyl chloride

Solution

Chlorobenzene is much less reactive than benzyl chloride in SN2. Isobutyl chloride is a primary halide while tert-butyl chloride is tertiary, so isobutyl is indeed more reactive — this pair is correct. 2-Chlorobutane and 3-Chlorobutane are both secondary, roughly equal. Option D lists the same compound twice.

Related JEE Advanced Chemistry questions

• When hydrogen halides react with alcohols, alkyl group rearrangement does not typically happen with most primary alcohols. What is the most accurate reason for this?
• Which of the following statements accurately describes the behavior of the given compound?
• Tertiary and secondary carbocations readily participate in elimination reactions when treated with strong alkoxide bases, while aryl and vinyl halides resist nucleophilic substitution. Which of the following reactions is correct?
• Although neopentyl alcohol is a primary alcohol, it follows the SN1 mechanism due to steric hindrance caused by a bulky alkyl group. Identify its structure.
• In the following sequence of reactions, identify the structures of intermediates Y, Z, W, and M: Y --(NaBH4)--> Z --(conc. HBr)--> W Y --(N2H4 / KOH, heat)--> M M --(NBS, heat/light)--> W W --(1) Mg/ether, (2) CO2, (3) H3O+)--> Ph-CH(COOH)-CH2-CH3 Which of the following statements about the intermediates is correct?
• Consider the compound CH3-CH2-CH(X)-CH3, where X is a halogen. When treated with alcoholic KOH and heated, it undergoes elimination to give alkene products. For which choice of X will the proportion of the Hofmann (less substituted) alkene product be the greatest?

⚔️ Practice JEE Advanced Chemistry free + battle 1v1 →