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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.

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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 of each reaction.

Draw the products formed when each compound is treated with HNO3 and H2SO4.

Draw the products formed when each compound is treated with HNO3 and H2SO4. State whether the reaction occurs faster or slower than a similar reaction with benzene.

Draw a stepwise mechanism for the sulfonation of an alkyl benzene such as A to form a substituted benzenesulfonic acid B. Treatment of B with base forms a sodium salt C that can be used as a synthetic detergent to clean away dirt (see Problem 3.22).

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,h谓

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