Benzyl bromide (C6H5CH2Br) reacts rapidly with CH3OH to afford benzyl methyl ether (C6H5CH2OCH3). Draw a stepwise mechanism for the reaction, and explain why this 1° alkyl halide reacts rapidly with a weak nucleophile under conditions that favor an SN1 mechanism. Would you expect the para-substituted benzylic halides CH3OC6H4CH2Br and O2NC6H4CH2Br to each be more or less reactive than benzyl bromide in this reaction? Explain your reasoning.

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
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.52P: Claisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads...
icon
Related questions
Question

Benzyl bromide (C6H5CH2Br) reacts rapidly with CH3OH to afford benzyl methyl ether (C6H5CH2OCH3). Draw a stepwise mechanism for the reaction, and explain why this 1° alkyl halide reacts rapidly with a weak nucleophile under conditions that favor an SN1 mechanism. Would you expect the para-substituted benzylic halides CH3OC6H4CH2Br and O2NC6H4CH2Br to each be more or less reactive than benzyl bromide in this reaction? Explain your reasoning.

Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Reactions at the Alpha Carbon Atom
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning