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Chapter 16: PROBLEM 16.13 (page 615)

Question: Use resonance theory explains why the labeled C-O bond lengths are equal in the acetate ion.

Short Answer

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Answer

Two equivalent resonance structures delocalize the pi bond and the negative charge.

Resonance theory of acetate ion

Step by step solution

01

Resonance theory of acetate ion

The resonance is the hypothetical state of a chemical species. Acetic acid loses a proton; the resulting acetate ion has a negative charge delocalized over both oxygen atoms.

The negative charge present at the oxygen atom is stabilized by delocalization.

02

Bond order of acetate ion

Each carbon-oxygen bond is halfway between a single bond and double bond and is said to have a bond order of 1.5.

The resonating structure of acetate ion:

Resoance structure

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Most popular questions from this chapter

Question:(a) Which triene has the largest heat of hydrogenation?(b) Which triene has the smallest heat of hydrogenation?(c) Which triene absorbs the longest wavelength of UV light?(d) Which triene is most reactive in the Diels-Alder reaction?

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