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Organic Chemistry

Leroy G. Wade

Chapter 17

Reactions Of Aromatic Compounds - all with Video Answers

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Section 1

Electrophilic Aromatic Substitution

02:20

Problem 1

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.

Bobby Barnes
Bobby Barnes
University of North Texas