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Chapter 22: Q85. (page 923)

Question: Draw a stepwise mechanism for the following reaction, a key step in the synthesis of linezolid, an antibacterial agent.

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01

Step-by-Step SolutionStep 1: Reaction with organolithium reagents

The polar organometallic compounds with a carbon-lithium bond, which are very strong bases, are called organolithium reagents. These transfer the organic group to the reacting compounds via deprotonation or nucleophilic addition reactions.

The 3-fluoro-4-morpholino phenyl carbamate is deprotonated in the presence of the organolithium reagent.

Deprotonation in the presence of RLi

02

Nucleophilic addition

The lone pair of electrons on the nitrogen atom attacks the electrophilic center, forming a C-N bond as the electrons shift towards the electronegative oxygen atom. The lone pair of electrons on oxygen attacks the carbonyl carbon resulting in ring closure to form the required antibacterial agent.

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Most popular questions from this chapter

Question: What products are formed by hydrolysis of each lactone or lactam with acid?

Question: What product is formed when the esters in ginkgolide B, the chapter-opening molecule, are hydrolyzed in aqueous acid? Indicate the stereochemistry of all stereogenic centers.

Ginkgolide B

Question: (a) Give an acceptable name for each compound. (b) Draw the organic products formed when A or B is treated with each reagent: [1]H3O+;[2]-OH,H2O;[3]CH3CH2CH2MgBr(excess), then H2O; [4] LiAlH4,ThenH2O, then .

What ester and Grignard reagent are needed to prepare each alcohol?

a.

b.

c.

Question: Give the structure corresponding to each name.

  1. cyclohexyl propanoate
  2. cyclohexanecarboxamide
  3. 4-methylheptanenitrile
  4. vinyl acetate
  5. benzoic propanoic anhydride
  6. 3-methylhexanoyl chloride
  7. octyl butanoate
  8. N,N-dibenzylformamide
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