Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 6 - Alkyl Halides: Nucleophilic Substitution and Elimination - Problems - Page 226: Problem 6-7

Answer

Hexane is in the top phase and water in the bottom phase because hexane is less dense than water. When water is shaken with chloroform, water will be in the top phase and chloroform will be in the bottom phase. Remember that alkyl chloride with 1 Cl atom is less dense than H2O while alkyl chloride with more than 1 Cl atom is more dense than H2O. Hexane has no halide atoms, and so is automatically less dense than H2O. But chloroform has 3 Cl atoms, so it is denser than H2O.

Work Step by Step

If water is shaken with ethanol, there will be no separate layers because ethanol is soluble in water. The OH in ethanol can form hydrogen bonding with water molecules.
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