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Chapter 6: 6-35b (page 181)

Follow the flow of electrons indicated by the curved arrows in each of the following polar reactions, and predict the products that result:

Short Answer

Expert verified

(b)

Curved arrow representation

Step by step solution

01

Attack of hydroxide ion

The hydroxide ion attacks the hydrogen of the methyl. This results in deprotonation to form water and a carbanion. Next, the bonding pair of electrons flow down from the carbon that had its hydrogen removed.

02

Formation of carbon-carbon double bond

These bonding pairs of electrons form a carbon-carbon double bond. This new bond forces the carbon-oxygen double bond to migrate up to the oxygen to form an oxyanion. The oxygen is negatively charged because wherever the arrow stop is where the charge ends up. Thus, the curved arrow representation is as shown:

curved arrow representation

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Most popular questions from this chapter

Radical chlorination of pentane is a poor way to prepare 1-chloropentane, but radical chlorination of neopentane,CH34C, is a good way to prepare neopentyl chloride,CH33CCH2Cl. Explain.

Look at the following energy diagram for an enzyme-catalyzed reaction:

(a) How many steps are involved?

(b) Which step is most exergonic?

(c) Which step is slowest?

An electrostatic potential map of boron trifluoride is shown. Is BF3likely to be a nucleophile or an electrophile? Draw a Lewis structure for BF3, and explain your answer.

Add curved arrows to the following polar reactions to indicate the flow of electrons in each:

(a)

(b)

Reaction of with 2-methylpropene yields 2-bromo-2-methylpropane. What is the structure of the carbocation formed during the reaction? Show the mechanism of the reaction.
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