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Chapter 15: Q 88p (page 737)

The intermediate shown here is formed during the hydroxide-ion-promoted hydrolysis of ester group. Propose a mechanism for the reaction.

Short Answer

Expert verified

When hydroxide ion attacks the N-H bond, electron delocalization occurs and water molecule is removed. Cyclisation also occurs.

Attack of hydroxide ion

Step by step solution

01

Step-by-Step SolutionStep1 : Attack of hydroxide ion 

When hydroxide ion attacks the N-H bond, electron delocalization occurs and water molecule is removed. Cyclisation also occurs.

Attack of hydroxide ion

02

Step 2: Attack of hydroxyl ion at carbonyl carbon

Hydroxyl ion is attacked at the carbonyl carbon, which release CF3CH2O-.

Attack of hydroxyl ion at carbonyl carbon

03

Attack of proton at N - C bond

Proton is attacked at the bond and electron delocalization occurs and the ring is opened.

Attack of proton at bond

04

Chirality of 3-methylpentan- 2,3- diol

Lastly, the water molecules are released by forming—a carboxylate anion.

Chirality of 3-methylpentan- 2,3- diol

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Most popular questions from this chapter

Describe how the target molecule (butanone) can be synthesized in a high yield from butane.

a. Which compound has the stretching vibration for its carbonyl group at the highest frequency: acetyl chloride, methyl acetate, or acetamide?

b. Which one has the stretching vibration for its carbonyl group at the lowest frequency?

How could you synthesize the following compounds starting with a carboxylic acid?

The H1NMR spectra for two esters with molecular formula C8H8O2 are shown next. Which of the esters is hydrolyzed more rapidly in an aqueous solution with a pH of 10?

When butanoic acid and 18O-labelled methanol react under acidic conditions, what compounds are labelled when the reaction has reached equilibrium?
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