Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Haloalkanes and Haloarenes

Question:

The number of mono bromo structural isomers formed by free radical bromination of isopentane are

Options:

4

2

1

3

Correct Answer:

4

Explanation:

The correct answer is Option (1) → 4

Isopentane is 2-methylbutane with structure:

$(CH_3)_2CH–CH_2–CH_3$

In free-radical bromination, substitution can occur at non-equivalent hydrogen atoms. Count the distinct types of hydrogens:

  1. Tertiary hydrogen
    – On the carbon attached to three other carbons (C-2) → 1 type
  2. Secondary hydrogens
    – On the CH₂ group → 1 type
  3. Primary hydrogens (two types)
    • Two equivalent CH₃ groups attached to C-2 → 1 type
    • One terminal CH₃ group → 1 different type

Total distinct positions =

1 (tertiary) + 1 (secondary) + 2 (primary) = 4

Hence, 4 mono-bromo structural isomers are formed.