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Chapter 15: Q72P (page 735)

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

Short Answer

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Mechanism followed as:

Step by step solution

01

Reaction of carboxylic acid with alcohol

When carboxylic acid reacts with alcohol formation of ester and the water occur and the oxygen of the carboxylic acid is leave in the form of water molecule.

02

Reaction of butanoic acid with methanol

when butanoic acid reacts with alcohol the carbonyl of the acid accepts the proton and then hydroxyl oxygen attack on carbonyl carbon followed by again protonation formation of -OH2 which is a best leaving group and that is the carboxylic acid oxygen which accepts the proton hence, labelled 18Ois present in the water

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Most popular questions from this chapter

Give two names for each of the following nitriles:

Propose a mechanism for the reaction of an acyl chloride with acetate ion to form an acid anhydride

Draw the structure for each of the following:

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

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

a. Propose a mechanism for the reaction of acetic anhydride with water.

b. How does this mechanism differ from the mechanism for the reaction of acetic anhydride with an alcohol?
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