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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

Draw the products formed when phenol ( C6H5OH) is treated with each set of reagents.

a. [1] HNO3, H2SO4; [2] Sn, HCl

b. [1] CH3CH22COCl,AlCl3; [2] Zn(Hg), HCl

c. [1] CH3CH2Cl,AlCl3; [2]Br2,hν

d. [1] CH32CHCl,AlCl3; [2] KMnO4

Draw the structure of A, an intermediate in the synthesis of the antipsychotic drug risperidone. Explain why three rings in risperidone are considered aromatic.

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