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 243: Problem 6-18

Answer

methyl iodide> methyl chloride> ethyl chloride> isopropyl bromide> neopentyl bromide> tert-butyl iodide

Work Step by Step

Methyl halides react fastest toward SN2 reaction. Methyl iodide reacts faster than methyl chloride because I- is much a better leaving group than Cl- (I- is larger and can let stabilize the negative charge better). After methyl chloride comes ethyl chloride because ethyl chloride is still a primary halide. Next is isopropyl bromide, which is a secondary halide. Neopentyl bromide follows. It is more reactive than tert-butyl iodide despite being bulkier than tert-butyl iodide. This is because neopentyl bromide is still a primary halide whereas tert-butyl iodide is a tertiary halide, which almost doesn't react toward SN2 at all.
Update this answer!

You can help us out by revising, improving and updating this answer.

Update this answer

After you claim an answer you’ll have 24 hours to send in a draft. An editor will review the submission and either publish your submission or provide feedback.