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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

Which compound in each pair is more reactive towards nucleophilic attack?

What Grignard reagent and carbonyl compound are needed to prepare each alcohol? As shown in part (d), 3o alcohols with three different R groups on the carbon bonded to the OH group can be prepared by three different Grignard reactions.

Question: How do the following experimental results support the resonance description of the relative stability of acid chlorides compared to amides? The C-Cl bond lengths in CH3Cl and CH3COCl are identical (178 pm), but the C-N bond in HCONH2 is shorter than the C-N bond in CH3NH2(135 pm versus 147 pm).

Draw the product formed when each organometallic reagent is treated with H2O.

Draw the products (including stereochemistry) of the following reactions.
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