An amide urther hydrolysis converts the amide As shown in parentheses in the two

Question

An amide urther hydrolysis converts the amide As shown in parentheses in the two equations, f to a carboxylic acid. Those descri The mechanism for the hydrolysis of a nitrile under acidic conditions is shown in Equation 18-25 ions are described in detail in Chapters 20 and 21 Mechanism for Equation 18-23 NH H20 (18-25) 3. Proton 1. Proton 2. Nucleophilic transfer c addition C transfer NH HQH2 NH2 +H 4. Proton 5. Proton CI transfer transfer c Although this mechanism consists of five elementary steps, the only step that a proton transfer is the nucleophilic addition step-Step 2. The four proton te t steps serve to add protons to N and remove them from O, making it possi is eat avoid gcnerating strongly basic species in the mechanism-a necessary condito y condition for 876 / CHAPTER 18 Nucleophilic Addition to Polar Bonds 2

Explanation / Answer

In any given reaction, under specific reaction conditions and reagents, the reactants tend to convert into more stable products via reactive intermediates.

For example in the above reaction of hydrolysis of nitriles in presence of acidic medium, the intermediate of the third step is imine intermediate.

With the acidic reaction environment imines are highly reactive (unstable), and hence the imine nitrogen gets protonated in the fourth step to give the more stable and less reactive amide product.

(knowing the functional group reactivities under given reaction conditions will help in what step or at which product reaction gets stopped)

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