Carboxylic acids (RCO 2 H; pKa ≈ 5) are approximately 10 11 times more acidic than alcohols (ROH; pKa ≈ 16). In other words using the concept of resonance the observation that a carboxylate (RCO 2 - ) ion is more stable than alkoxide (RO - ) ion is to be explained. Concept introduction: Carboxylic acids are more acidic since their conjugate bases obtained by the loss of a proton, carboxylate anions, are stablised by resonance. Alcohols are less acidic as there is no resonance stabilization possible in their conjugate bases, the alkoxide ions.

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Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 10.SE, Problem 46AP

Interpretation Introduction

Interpretation:

Carboxylic acids (RCO₂H; pKa ≈ 5) are approximately 10¹¹ times more acidic than alcohols (ROH; pKa ≈ 16). In other words using the concept of resonance the observation that a carboxylate (RCO₂^-) ion is more stable than alkoxide (RO^-) ion is to be explained.

Concept introduction:

Carboxylic acids are more acidic since their conjugate bases obtained by the loss of a proton, carboxylate anions, are stablised by resonance. Alcohols are less acidic as there is no resonance stabilization possible in their conjugate bases, the alkoxide ions.

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Which of the ff statements is false? In aqueous solution the order of base strength R3N > R2NH > RNH2 > NH3. Alkyl groups increase the electron density on nitrogen, making the amine more basic. Alkyl groups stabilize the positive charge on the conjugate acid making the ammonium ion less acidic. Solvation through H-bonding with water is more important in the conjugate acid than in the free amine.

Which is a stronger acid and has the most stable conjugate base? Estimate the pKA values for both compounds.

Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 10.SE, Problem 46AP

Interpretation Introduction

Interpretation:

Carboxylic acids (RCO₂H; pKa ≈ 5) are approximately 10¹¹ times more acidic than alcohols (ROH; pKa ≈ 16). In other words using the concept of resonance the observation that a carboxylate (RCO₂^-) ion is more stable than alkoxide (RO^-) ion is to be explained.

Concept introduction:

Carboxylic acids are more acidic since their conjugate bases obtained by the loss of a proton, carboxylate anions, are stablised by resonance. Alcohols are less acidic as there is no resonance stabilization possible in their conjugate bases, the alkoxide ions.

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 10.SE, Problem 46AP

Interpretation Introduction

Interpretation:

Carboxylic acids (RCO₂H; pKa ≈ 5) are approximately 10¹¹ times more acidic than alcohols (ROH; pKa ≈ 16). In other words using the concept of resonance the observation that a carboxylate (RCO₂^-) ion is more stable than alkoxide (RO^-) ion is to be explained.

Concept introduction:

Carboxylic acids are more acidic since their conjugate bases obtained by the loss of a proton, carboxylate anions, are stablised by resonance. Alcohols are less acidic as there is no resonance stabilization possible in their conjugate bases, the alkoxide ions.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 10.SE, Problem 46AP

Interpretation Introduction