The reaction of 10 with ethylene glycol and p-toluenesulfonic acid (p-TSOH, shown) in boiling toluene gives 11: LOME OMe но он Me Toluene Me OH (TSOH) 10 11 Propose a reasonable mechanism for this transformation. Classify the cyclization steps according to Baldwin rules (for example, a "5-exo-dig" cyclization).

The reaction of 10 with ethylene glycol and p-toluenesulfonic acid (p-TSOH, shown) in boiling toluene gives 11: LOME OMe но он Me Toluene Me OH (TSOH) 10 11 Propose a reasonable mechanism for this transformation. Classify the cyclization steps according to Baldwin rules (for example, a "5-exo-dig" cyclization).

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.39P: Following are diastereomers (A) and (B) of 3-bromo-3,4-dimethylhexane. On treatment with sodium...

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