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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鈥攁 carboxylate anion.

Chirality of 3-methylpentan- 2,3- diol

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Most popular questions from this chapter

There are three carbon鈥搊xygen bonds in methyl acetate.

a.What are their relative bond lengths?

b.What are the relative infrared (IR) stretching frequencies of these bonds?

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

Write the mechanism for the acid-catalyzed reaction of an amide with an alcohol to form an ester.

Draw the structure for each of the following:

\(\begin{array}{}a.{\rm{ phenyl acetate}}\\b.{\rm{ }}\gamma {\rm{ - caprolactam}}\\c.{\rm{ sodium formate}}\\d.{\rm{ N - benzylethanamide}}\\e.{\rm{ }}\gamma {\rm{ - methylcaproic acid}}\\f.{\rm{ }}\beta {\rm{ - bromobutyramide}}\\g.{\rm{ ethyl 2 - chloropentanoate}}\\h.{\rm{cyclohexanecarbonyl chloride}}\\i.{\rm{ }}\alpha {\rm{ - chlorovaleric acid}}\\\end{array}\)

How could you use 1H NMR spectroscopy to distinguish the following esters?
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