Bromo compound N can undergo substitution with nucleophiles X to give mixtures of products O and P as shown below. Explain how this is possible, and suggest an explanation for the observation that the proportion of product P increases with increasing solvent polarity. F N "Br X™ F P

Bromo compound N can undergo substitution with nucleophiles X to give mixtures of products O and P as shown below. Explain how this is possible, and suggest an explanation for the observation that the proportion of product P increases with increasing solvent polarity. F N "Br X™ F P

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

Chapter11: Ethers, Epoxides, And Sulfides

Section: Chapter Questions

Problem 11.18P

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Question

Bromo compound N can undergo substitution with nucleophiles X to give mixtures of products
O and P as shown below. Explain how this is possible, and suggest an explanation for the
observation that the proportion of product P increases with increasing solvent polarity.
F
N
Br
X-
O
X
...X
F
P

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