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Chapter 7: PROPBLEM 7.9 (page 255)

Question: What neutral nucleophile is needed to convert dihalide A to ticlopidine, an antiplatelet drug used to reduce the risk of strokes?

Short Answer

Expert verified

The structure of the neutral nucleophile is shown below:

Step by step solution

01

Nucleophilic substitution reaction

A nucleophilic substitution reaction is similar to an acid-base reaction. In this reaction, the nucleophile acts as a base and donates electrons to the electrophile.

02

Reaction of Lewis base and Lewis acid

The complete reaction is shown below:

Attack of the nucleophile on the electrophile

In the above reaction, the lone pair of N (Lewis base) donates its electron pair to the electrophilic carbon atom of 1-chloro-2-(chloromethyl)benzene (Lewis acid). This leads to the removal of the chlorine group.

After that, the proton is transferred to form ticlopidine. Thus, the structure of the neutral nucleophile is shown below:

Structure of nucleophile

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Most popular questions from this chapter

Question: What happens to the rate of an SN2 reaction under each of the following conditions?

a. [RX] is tripled, and:Nu- stays the same.

b. Both [RX] and role="math" localid="1648206216789" :Nu-are tripled.

c. [RX] is halved, androle="math" localid="1648206048742" :Nu-stays the same.

d. [RX] is halved, and role="math" localid="1648206067374" :Nu-is doubled.

Question: Rank the nucleophiles in each group in order of increasing nucleophilicity.

a. OH-,NH2- , H2O

b. OH- ,Br- , F-(polar aprotic solvent)

c. H2O, OH-,CH3CO2-

Question: When trichloride J is treated with CH3OH , nucleophilic substitution forms the dihalide K. Draw a mechanism for this reaction and explain why one Cl is much more reactive than the other two Cl’s so that a single substitution product is formed.

Question: Which compound in each pair undergoes a faster SN2 reaction?

a.

and

b.

and

Question: What nucleophile is needed to convert to each product?

a.


b.


c.

d.
See all solutions

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