Organic Chemistry (8th Edition)

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

Chapter 10 - Structure and Synthesis of Alcohols - Problems - Page 436: Problem 10-7 b

Answer

2-chloropropan-1-ol

Work Step by Step

2-chloropropan-1-ol is more acidic because the Cl is more close to the OH in 2-chloropropan-1-ol than in 3-chloropropan-1-ol. The electron withdrawing chlorine helps to stabilize the 2-chloroethoxide ion, making it more acidic.
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