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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: Chondrocole A is a marine natural product isolated from red seaweed that grows in regions of heavy surf in the Pacific Ocean. (a) Predict the solubility of chondrocole A in water and . (b) Locate the stereogenic centers and label each as R or S. (c) Draw a stereoisomer and a constitutional isomer of chondrocole A.

Question: Why is the amine N atom more nucleophilic than the amide N atom CH3CONHCH2CH2CH2NHCH3?

Question: Nicotine, a toxic and addictive component of tobacco, is synthesized from A using SAM. Write out the reaction that converts A into nicotine.

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: Draw the products (including stereochemistry) for each reaction.

a.

b.
See all solutions

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