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For the following compounds, write the conjugate base that would result if the labeled proton were removed. Include resonance structures if there are any. Indicate which of the two labeled protons you expect to be more acidic and why. a) b) На H. На c) Ha H d) -Hp H H

For the following compounds, write the conjugate base that would result if the labeled proton were removed. Include resonance structures if there are any. Indicate which of the two labeled protons you expect to be more acidic and why. a) b) На H. На c) Ha H d) -Hp H H

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Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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1. For the following compounds, write the conjugate base that would result if the labeled proton were removed. Include resonance structures if there are any. Indicate which of the two labeled protons you expect to be more acidic and why. a) A compound with two labeled protons \(H_a\) and \(H_b\). The structure includes an alkene and an alkyne. b) A compound featuring a benzene ring attached to an ester group, with labeled protons \(H_a\) on the oxygen and \(H_b\) on the ethoxy group. c) A structure containing an imine with \(H_a\) on the carbon attached to nitrogen and \(H_b\) on the nitrogen itself. d) A diketone structure with \(H_a\) and \(H_b\) on the carbon adjacent to the ketone groups. ### Analysis: - **a)** More acidic proton likely depends on hybridization (alkyne \(H_b\) is often more acidic due to sp hybridization). - **b)** Consider resonance stabilization for \(H_a\) (phenoxide ion) vs. \(H_b\); typically \(H_a\) is more acidic because of resonance. - **c)** Imine nitrogen proton \(H_b\) may have different acidity due to resonance or electron-withdrawing effects from nitrogen. - **d)** \(H_b\) near carbonyl groups might be more acidic because of resonance and inductive effects.
Transcribed Image Text:1. For the following compounds, write the conjugate base that would result if the labeled proton were removed. Include resonance structures if there are any. Indicate which of the two labeled protons you expect to be more acidic and why. a) A compound with two labeled protons \(H_a\) and \(H_b\). The structure includes an alkene and an alkyne. b) A compound featuring a benzene ring attached to an ester group, with labeled protons \(H_a\) on the oxygen and \(H_b\) on the ethoxy group. c) A structure containing an imine with \(H_a\) on the carbon attached to nitrogen and \(H_b\) on the nitrogen itself. d) A diketone structure with \(H_a\) and \(H_b\) on the carbon adjacent to the ketone groups. ### Analysis: - **a)** More acidic proton likely depends on hybridization (alkyne \(H_b\) is often more acidic due to sp hybridization). - **b)** Consider resonance stabilization for \(H_a\) (phenoxide ion) vs. \(H_b\); typically \(H_a\) is more acidic because of resonance. - **c)** Imine nitrogen proton \(H_b\) may have different acidity due to resonance or electron-withdrawing effects from nitrogen. - **d)** \(H_b\) near carbonyl groups might be more acidic because of resonance and inductive effects.
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