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Chapter 18: 25 P (page 708)

Draw a stepwise mechanism for the following reaction that forms ether D. D can be converted to the antidepressant fluoxetine (trade name Prozac) in a single step.

Short Answer

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Stepwise mechanism

Step 1.

Step 2.

Step 3.

Step by step solution

01

Reaction of aryl halides

Aryl halides having strong electron-withdrawing groups on the ortho or para positions react with nucleophiles to give substitution products.

They are inert for SN1and SN2mechanism and hence follow SNAr(addition-elimination) mechanism.

02

Mechanism

  • Tertiary butoxide ion acts as a base.

Proton is abstracted from an alcoholic group of 3-(dimethylamino)-1-phenylpropan-1-ol to form its conjugate base.

  • The conjugate base of 3-(dimethylamino)-1-phenylpropan-1-ol reacts with 1-chloro-4-(trifluoromethyl) benzene to form more stable resonance contributors.

  • The resonance stabilized carbanion undergoes an elimination reaction and forms the required compound D.

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Most popular questions from this chapter

Question: The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown.

a. Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole.

b. Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline.

c. Explain why electrophilic substitution occurs more readily at C3 rather than C2 of indole.

You have learned two ways to make an alkyl benzene: Friedel–Crafts alkylation, and Friedel–Crafts acylation followed by reduction. Although some alkyl benzenes can be prepared by both methods, it is often true that only one method can be used to prepare a given alkyl benzene. Which method(s) can be used to prepare each of the following compounds from benzene? Show the steps that would be used.

Devise a synthesis of each compound from the indicated starting material.

Question: Carboxylic acid X is an intermediate in the multistep synthesis of proparacaine, a local anesthetic. Devise a synthesis of X from phenol and any needed organic or inorganic reagents.

Draw the products of each reaction.
See all solutions

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