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Chapter 12: Q40E (page 354)

Base treatment of the following α,β-unsaturated carbonyl compound yields an anion by removal of H+ from theγcarbon. Why are hydrogens on theγcarbon atom acidic?

Short Answer

Expert verified

In this compound γ-carbon loses its hydrogen atom to reduce positive charge and increase stability, and make it more acidic.

Step by step solution

01

Resonance structure of the compound

The resonance structures of the yield compound are,

Resonance forms of the given compound

02

Determination of hydrogens on the g carbon atom is acidic

In enolate, the α-carbon is deprotonated which is stabilized by the resonance structure. In that structure, the negative charge is localised on electronegative O-atom.

In this compound, α,β-unsaturated carbonyl compound is deprotonated on γ-carbon. The resonance of this compound localise the negative charge on the oxygen atom.

In this compound γ-carbon loses its hydrogen atom and make it more acidic.

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Most popular questions from this chapter

The infrared spectrum of the compound with the mass spectrum shown below lacks any significant absorption above 3000cm-1 . There is a prominent peak near 1740cm-1 and another strong peak near 1200cm-1 .

Propose a structure consistent with the data.

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