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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

One consequence of the base-catalyzed isomerization of unsaturated ketones described in Problem 22-55 is that 2-substituted 2-cyclopentenones can be interconverted with 5-substituted 2-cyclopentenones. Propose a mechanism for this isomerization.

Question: Why do you suppose accidental overlap of signals is much more common in1H NMR than in13C NMR?

The Favorskii reactioninvolves the treatment of an -bromo ketone with a base to yield a ring-contracted product. For example, the reaction of 2-bromocyclohexanone with aqueous NaOH yields cyclopentanecarboxylic acid. Propose a mechanism.

Assign Cahn–Ingold–Prelog rankings to the following sets of substituents

a.−CH=CH2,−CH(CH3)2,−C(CH3)3,−CH2CH3

b.−CO2CH3,−COCH3,−CH2OCH3,−CH2CH3

c.−CO2CH3,−COCH3,−CH2OCH3,−CH2CH3

d.−CO2CH3,−COCH3,−CH2OCH3,−CH2CH3,−CO2CH3,−COCH3,−CH2OCH3,−CH2CH3

From what alkyne might each of the following substances have been made? (Green = Cl.)
See all solutions

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