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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

a. What species other than an acid can be used to increase the rate of the transesterification reaction that converts methyl acetate to propylacetate?

b. Explain why the rate of aminolysis of an ester cannot be increased by H+, HO-, or RO-.

If propionyl chloride is added to one equivalent of methylamine, only a 50% yield of N-methylpropanamide is obtained. If, however, the acyl chloride is added to two equivalents of methylamine, the yield of N-methylpropanamide is almost 100%. Explain these observations.

An aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major product. However, if the amine is tertiary, an amide is not formed. What product isformed? Explain.

Question: What product do you expect to obtain from each of the following reactions?

a.

b.

Give two names for each of the following nitriles:
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