Chapter 9: Free Radical Substitution Reaction of Alkanes

Answers to Chapter 9 Practice Questions

9.1 Predict the percentage yield of each product for the monochlorination of isobutane by calculation and compare your calculated numbers to the experiment results. Are they consistent?

isopropane with Cl2 in the presence of delta/hv produces 63% and 37% experimental results


The amount of 1°-chloride: 9 (number of 1°hydrogens) × 1.0 (relative reactivity) = 9.0

The amount of 3°-chloride: 1 (number of 3°hydrogens) × 3.8 (relative reactivity) = 3.8

yield% of 1°-chloride:  8.0/12.8 = 70.3%

yield% of 3°-chloride 3.8/12.8 = 29.7%

The calculated values are consistent with the experiment results, but not exactly the same though.

9.2 Show the major bromination product of the following reactions.

9.3 Show all the mono-chlorination products of butane with any stereoisomers when applied.


9.4 Design the synthesis route.


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