At 600 C, the ratio of the relative rates of formation of a tertiary, a secondary, and

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At 600 °C, the ratio of the relative rates of formation of a tertiary, a secondary, and a primary radical by a chlorine radical is 2.6:2.1:1. Explain the change in the degree of regioselectivity compared with what Dr. Al Cahall found in Problem 17.


Problem 17

Dr. Al Cahall wanted to determine experimentally the relative ease of removal of a hydrogen atom from a tertiary, a secondary, and a primary carbon by a chlorine radical. He allowed 2-methylbutane to undergo chlorination at 300 °C and obtained as products 36% 1-chloro-2-methylbutane, 18% 2-chloro-2-methylbutane, 28% 2-chloro-3-methylbutane, and 18% 1-chloro-3-methylbutane. What values did he obtain for the relative ease of removal of tertiary, secondary, and primary hydrogen atoms by a chlorine radical under the conditions of his experiment?

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Organic Chemistry

ISBN: 978-0131407480

4th edition

Authors: Paula Yurkanis Bruice

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