Step 2 of the iodination of benzene shows water acting as a base and removing a proton from the sigma complex. We did notconsider the possibility of water acting as a nucleophile and attacking the carbocation, as in an electrophilic addition to an alkene.Draw the reaction that would occur if water reacted as a nucleophile and added to the carbocation. Explain why this type ofaddition is rarely observed.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
Problem 26E
icon
Related questions
Question

Step 2 of the iodination of benzene shows water acting as a base and removing a proton from the sigma complex. We did not
consider the possibility of water acting as a nucleophile and attacking the carbocation, as in an electrophilic addition to an alkene.
Draw the reaction that would occur if water reacted as a nucleophile and added to the carbocation. Explain why this type of
addition is rarely observed.

Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 3 images

Blurred answer
Knowledge Booster
Selection Rules for Pericyclic Reactions
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: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Chemistry for Today: General, Organic, and Bioche…
Chemistry for Today: General, Organic, and Bioche…
Chemistry
ISBN:
9781305960060
Author:
Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:
Cengage Learning
Pushing Electrons
Pushing Electrons
Chemistry
ISBN:
9781133951889
Author:
Weeks, Daniel P.
Publisher:
Cengage Learning