JEE Main 2021 · 25 July · evening · Single correct · +4 / −1

The correct decreasing order of densities of the following compounds is :

JEE Main PYQ figure
  1. (a) (D) > (C) > (B) > (A)
  2. (b) (C) > (D) > (A) > (B)
  3. (c) (C) > (B) > (A) > (D)
  4. (d) (A) > (B) > (C) > (D)
Answer and solution

Answer (a) (D) > (C) > (B) > (A)

Solution

Chemistry ma’am · 3 steps

The ring stays the same size, so every heavier halogen you add packs more mass into nearly the same space.

  1. What sets density. All four molecules are built on the same benzene ring, so they take up roughly similar volumes. Density is mass per volume, so it rises with the mass of the atoms attached to the ring.
  2. Halogens add mass. Swapping a light H (mass 1) for Cl (35.5) or Br (80) adds a lot of mass and only a little volume. So more halogen atoms, and heavier ones, mean a denser liquid.
    CompoundGroups on the ringMolar mass (g mol⁻¹)Density (about, g cm⁻³)
    (D) 1-bromo-3-chlorobenzeneBr + Cl191.51.63
    (C) 1,3-dichlorobenzeneCl + Cl1471.29
    (B) chlorobenzeneCl112.51.11
    (A) benzenenone780.88
  3. So. Density falls as the halogen load falls: (D) > (C) > (B) > (A), which is option (a).

The idea to keep. For haloarenes and haloalkanes on the same skeleton, density goes up with the number of halogens and with their atomic mass: I > Br > Cl > F. Benzene with no halogen is lighter than water.

Answer from the NTA final answer key. Solution by PrepWiser.

Study Halogen Derivatives — Haloalkanes & Haloarenes

Asked about 120 times in JEE Main since 2020. This question is from 2021.