
(a)
Interpretation:
To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting
Concept introduction:
Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the
Symmetrical ketone=Symmetrical
Unsymmetrical Ketone=Unymmetrical
To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.
(b)
Interpretation:
To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.
Concept introduction:
Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the
Symmetrical ketone=Symmetrical
Unsymmetrical Ketone=Unymmetrical
To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.
(c)
Interpretation:
To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.
Concept introduction:
Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the
Symmetrical ketone=Symmetrical
Unsymmetrical Ketone=Unymmetrical
To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.
(d)
Interpretation:
To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.
Concept introduction:
Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the
Symmetrical ketone=Symmetrical
Unsymmetrical Ketone=Unymmetrical
To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

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Chapter 22 Solutions
Student Study Guide and Solutions Manual T/A Organic Chemistry
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- Identifying electron-donating and For each of the substituted benzene molecules below, determine the inductive and resonance effects the substituent will have on the benzene ring, as well as the overall electron-density of the ring compared to unsubstituted benzene. Molecule Inductive Effects NH2 ○ donating NO2 Explanation Check withdrawing no inductive effects Resonance Effects Overall Electron-Density ○ donating O withdrawing O no resonance effects O donating O withdrawing O donating withdrawing O no inductive effects Ono resonance effects O electron-rich electron-deficient O similar to benzene O electron-rich O electron-deficient O similar to benzene olo 18 Ar 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibilityarrow_forwardRank each of the following substituted benzene molecules in order of which will react fastest (1) to slowest (4) by electrophilic aromatic substitution. Explanation Check Х (Choose one) OH (Choose one) OCH3 (Choose one) OH (Choose one) © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Centerarrow_forwardAssign R or S to all the chiral centers in each compound drawn below porat bg 9 Br Brarrow_forward
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