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Chapter 12: 38E (page 385)

Which is stronger, the C=O bond in an ester () or the C=O bond in a saturated ketone ()? Explain

Short Answer

Expert verified

An ester C=O bondis stronger than a saturated ketone C=O bond.

Step by step solution

01

Energy

Energy is directly related to frequency and inversely related to wavelength. But in the case of wavenumber, energy is directly related to wavenumber.

02

Fundamentals to decide stronger bond

As the wavenumber increases, the energy needed to cause IR absorption increases, indicating greater bond strength.

03

Strength of ester and saturated ketone

The ester stretch occurs at higher wavenumbers and, therefore, higher energies. Since more energy is required to stretch that bond, the ester bond must be stronger.

Thus, an ester C=O bondis stronger than a saturated ketone C=O bond,respectively.

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Most popular questions from this chapter

As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich Wohler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone.

(a) What is a likely structure for the keto acid?

(b) What is a likely structure for ecgonine, neglecting stereochemistry?

(c) What is a likely structure for cocaine, neglecting stereochemistry?

Question: How might you use IR spectroscopy to distinguish between the following pairs of isomers?

a)CH3CH2OHandCH3OCH3b)cyclohexaneand1-hexenec)CH3CH2CO2HandHOCH2CH2CHO

The infrared spectrum of the compound with the mass spectrum shown below has strong absorbances at 1584, 1478, and 1446 cm-1 . Propose a

structure consistent with the data.

Question: Grignard reagents undergo a general and very useful reaction with

ketones. Methylmagnesium bromide, for example, reacts with cyclohexanoneto yield a product with the formulaC7H14O . What is the structure of this product if it has an IR absorption at 3400cm-1?

Propose structures for compounds that meet the following descriptions:

  1. An optically active compound C5H10Owith an IR absorption at 1730 cm-1.
  2. A non-optically active compound C5H9N with an IR absorption at 2215cm-1.
See all solutions

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