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Step 2 of the iodination of benzene shows water acting as

Chapter 11, Problem 1P

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QUESTION:

Problem 1P

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.

ANSWER:

Solution 1P

 Water reacted as a nucleophile and added to the carbocation.

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