Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 23.2, Problem 5P

Instead of adding to the 4a position and protonating N-5, the thiolate ion could have added to the 10a position and protonated N-l. (The numbering system is on page 1071.) Why is addition to the 4a position favored? (Hint: Which nitrogen is a stronger base?)

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Organic Chemistry (8th Edition)

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