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Chapter 15: Q29P (page 708)

Problem:D. N. Kursanov, a Russian chemist, proved that the bond that is broken in the hydroxide-ion-promoted hydrolysis of an ester is the acyl C-O bond, rather than the alkyl C-O bond, by studying the hydrolysis

of the following ester under basic conditions:

a. What products contained the label?

b. What product would have contained the label if the alkyl C-O bond had broken?

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Isotope labeling

Isotope labeling is the method in which theatom in a chemical compound is replaced by its isotopeexample are as follows:

  • Replacing hydrogen with its isotope deuterium
  • Replacing 16O with its isotope 18O

The isotope labeling method detects which chemical bond breaks when the reaction occurs by determining which atom in the product the labeled isotope is found.

02

18O  label product

The hydroxide ion promoter hydrolysis of given ester ethyl propionate results in carboxylic acid and alcohol formation.

  1. When the isotope-labeled () ester ethyl propionate acyl C-O bond is broken, it results in a butanoic acid (carboxylic acid) formation in which oxygen is labeled (); the structure is shown as follows.


Butanoic acid labeled with 18O

B.. When the isotope-labeled (18O ) ester ethyl propionate alkyl C-O bond is broken, resulting in an ethanol (alcohol) formation in which oxygen is labeled ( 18O ); the structure is shown as follows:

Ethanol labelled with18O

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Most popular questions from this chapter

When treated with an equivalent of methanol, compound A, with the molecular formula C4H6Cl2O, forms the compound whose 1H NMR spectrum is shown here. Identify compound A.

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-.

What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?

  1. Pentylamine

  2. Iso hexyl amine

  3. Benzylamine

  4. Cyclohexylamine

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 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?
See all solutions

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