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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: Give the IUPAC name for each compound, including any R,S designation.

a.

b.

Question: Which is the better leaving group in each pair?

a.Cl-,I-

b. NH3,NH2

c. H2O,H2S

Question: What is the likely mechanism of nucleophilic substitution for each alkyl halide?

a.

b.

c.

d.

Question: Which solvents favor SN1reactions and which favor SN2 reactions?

a.

b. CH3CN

c.

d.

Question: Pick the reactant or solvent in each part that gives the faster SN1 reaction.

  1. Reaction of H2O with (CH3)CCl or (CH3)3Cl
  2. Reaction of CH3OH with (CH3)CBr or (CH3)2CHCH2Br
  3. Reaction of CH3CH2CH(I)CH3with CH3CH2OH in water or DMSO
See all solutions

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