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Chapter 9: Q20P (page 411)

Draw the configuration(s) of the substitution product(s) formed from the reaction of the following compounds with the indicated nucleophiles:

Short Answer

Expert verified

a)

It follows SN2 mechanism.

b.

It follows SN2 mechanism.

Step by step solution

01

How SN2 reaction proceed

1. It is one step reaction.

2. In this nucleophile attacks the back side of the carbon.

3. In this one intermediate stage is formed.

4. In intermediate stage one group is leaving group and one group is attacking group.

5. In this inversion of reaction takes place.

02

Final answer

a)

It follows the SN2 mechanism.

b)

It follows SN2 mechanism.

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Most popular questions from this chapter

A chemist wanted to synthesize the aesthetic 2-ethoxy-2-methylpropane. He used ethoxide ion and 2-chloro-2-methylpropane for his synthesis and ended up with no ether. What was the product of his synthesis? What reagents should he have used?

a. Which is a stronger base: RO- or RS-?

b. Which is a better nucleophile in an aqueous solution?

c. Which is a better nucleophile in DMSO?

Two elimination products are obtained from the following E2 reaction

a. What are the elimination products?

b. Which is formed in greater yield? (Hint:See Problem 91.)

Draw the products of each of the following SN2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

a.(3S,4S)-3-bromo-4-methylhexane + CH3O-

b.(3R,4R)-3-bromo-4-methylhexane + CH3O-

c.(3S,4R)-3-bromo-4-methylhexane + CH3O-

d.(3R,4S)-3-bromo-4-methylhexane + CH3O-

Which member in each pair in Problem 68 is a better leaving group?
See all solutions

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