Fundamentals of General, Organic, and Biological Chemistry (8th Edition)
Fundamentals of General, Organic, and Biological Chemistry (8th Edition)
8th Edition
ISBN: 9780134015187
Author: John E. McMurry, David S. Ballantine, Carl A. Hoeger, Virginia E. Peterson
Publisher: PEARSON
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Chapter 17, Problem 17.30UKC

(a)

Interpretation Introduction

Interpretation:

The reason for using the terms pyruvate and lactate rather than pyruvic acid and lactic acid at pH=7.4 has to be explained.

Concept Introduction:

Carboxylic acid: One OH group is attached to the carbonyl carbon atom of the compound. It is represented as RCOOH

Carboxylate anion: They are anions formed when hydrogen atom is removed from the COOH group of carboxylic acid. It forms an equilibrium with carboxylic acid in an aqueous solution.

(a)

Expert Solution
Check Mark

Answer to Problem 17.30UKC

At pH=7.4, pyruvic acid and lactic acid exist as anions(pyruvate and lactate)

Explanation of Solution

Carboxylate anions are anions formed when hydrogen atom is removed from the COOH group of carboxylic acid. It forms an equilibrium with carboxylic acid in an aqueous solution.

At pH=7.4, pyruvic acid and lactic acid exist as anions where hydrogen atom is removed from the COOH group.

Therefore,

At pH=7.4 pyruvate and lactate exist.

(b)

Interpretation Introduction

Interpretation:

The structures acid altered to create pyruvic and lactic acid has to be drawn.

Concept Introduction:

Carboxylic acid: One OH group is attached to the carbonyl carbon atom of the compound. It is represented as RCOOH

Carboxylate anion: They are anions formed when hydrogen atom is removed from the COOH group of carboxylic acid. It forms an equilibrium with carboxylic acid in an aqueous solution.

(b)

Expert Solution
Check Mark

Answer to Problem 17.30UKC

The altered structure is

Fundamentals of General, Organic, and Biological Chemistry (8th Edition), Chapter 17, Problem 17.30UKC , additional homework tip  1

Explanation of Solution

Carboxylate anions are anions formed when hydrogen atom is removed from the COOH group of carboxylic acid. It forms an equilibrium with carboxylic acid in an aqueous solution.

To alter the structures of pyruvate and lactate to create pyruvic acid and lactic acid, one hydrogen atom is added to the COO group.

Therefore,

The structures acid altered to create pyruvic and lactic acid are,

Fundamentals of General, Organic, and Biological Chemistry (8th Edition), Chapter 17, Problem 17.30UKC , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:

The hydrogen bonding in pyruvate and lactate has to be drawn. The expected difference in the solubility of pyruvate and lactate in water has to be explained.

Concept Introduction:

Solubility: The maximum quantity of a solute which can be dissolved at a particular amount of solvent in a certain temperature.

Carboxylic acid: One OH group is attached to the carbonyl carbon atom of the compound. It is represented as RCOOH

Carboxylate anion: They are anions formed when hydrogen atom is removed from the COOH group of carboxylic acid. It forms an equilibrium with carboxylic acid in an aqueous solution.

Hydrogen bonding is a type of dipole-dipole interaction of molecules when the hydrogen is bonded to strong electronegative atom in the molecules.

(c)

Expert Solution
Check Mark

Answer to Problem 17.30UKC

  • The solubilities of pyruvate and lactate in water is similar.
  • Hydrogen bonding in pyruvate,

Fundamentals of General, Organic, and Biological Chemistry (8th Edition), Chapter 17, Problem 17.30UKC , additional homework tip  3

  • Hydrogen bonding in lactate,

Fundamentals of General, Organic, and Biological Chemistry (8th Edition), Chapter 17, Problem 17.30UKC , additional homework tip  4

Explanation of Solution

Hydrogen bonding is a type of dipole-dipole interaction of molecules when the hydrogen is bonded to strong electronegative atom in the molecules.

  • The oxygen atom in the COO group of pyruvate and lactate forms hydrogen bond with the hydrogen atom of water molecule.
  • The hydrogen atom in the OH group present in the lactate forms hydrogen bonding with oxygen atom of water molecule whereas oxygen atom on the carbonyl carbon present in the pyruvate forms hydrogen bonding with hydrogen atom of water molecule
  • Since both pyruvate and lactate can form hydrogen bond with water molecule, they are soluble in water. The solubilities of pyruvate and lactate in water is similar.

Hydrogen bonding in pyruvate,

Fundamentals of General, Organic, and Biological Chemistry (8th Edition), Chapter 17, Problem 17.30UKC , additional homework tip  5

Hydrogen bonding in lactate,

Fundamentals of General, Organic, and Biological Chemistry (8th Edition), Chapter 17, Problem 17.30UKC , additional homework tip  6

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Chapter 17 Solutions

Fundamentals of General, Organic, and Biological Chemistry (8th Edition)

Ch. 17.1 - Prob. 17.11PCh. 17.1 - Prob. 17.12PCh. 17.1 - Prob. 17.13KCPCh. 17.2 - Salsalate, which is an ester formed by the...Ch. 17.2 - Prob. 17.2CIAPCh. 17.2 - Prob. 17.3CIAPCh. 17.2 - Prob. 17.14PCh. 17.2 - Prob. 17.15PCh. 17.2 - Prob. 17.16PCh. 17.3 - Prob. 17.17PCh. 17.3 - Raspberry oil contains an ester that is made by...Ch. 17.3 - Prob. 17.19PCh. 17.3 - Prob. 17.20PCh. 17.3 - Prob. 17.21PCh. 17.4 - If a bottle of aspirin tablets has the aroma of...Ch. 17.4 - Prob. 17.23PCh. 17.4 - What carboxylic acids and amines result from...Ch. 17.5 - Prob. 17.25PCh. 17.5 - Prob. 17.26KCPCh. 17.6 - Prob. 17.27PCh. 17.6 - Prob. 17.28PCh. 17.6 - Prob. 17.4CIAPCh. 17.6 - Prob. 17.5CIAPCh. 17.6 - Prob. 17.29PCh. 17 - Prob. 17.30UKCCh. 17 - Prob. 17.31UKCCh. 17 - One phosphorylated form of glycerate is...Ch. 17 - Prob. 17.33UKCCh. 17 - Prob. 17.34UKCCh. 17 - Prob. 17.35UKCCh. 17 - Prob. 17.36UKCCh. 17 - For the following compounds, give the systematic...Ch. 17 - Write the equation for the ionization of hexanoic...Ch. 17 - Prob. 17.39APCh. 17 - Prob. 17.40APCh. 17 - Prob. 17.41APCh. 17 - Give systematic names for the following carboxylic...Ch. 17 - Give systematic names for the following carboxylic...Ch. 17 - Prob. 17.44APCh. 17 - Prob. 17.45APCh. 17 - Draw structures corresponding to the following...Ch. 17 - Draw structures corresponding to the following...Ch. 17 - Malic acid, a dicarboxylic acid found in apples,...Ch. 17 - Prob. 17.49APCh. 17 - Prob. 17.50APCh. 17 - Prob. 17.51APCh. 17 - Prob. 17.52APCh. 17 - Prob. 17.53APCh. 17 - Give systematic names for the following structures...Ch. 17 - Give systematic names for the following structures...Ch. 17 - Prob. 17.56APCh. 17 - Prob. 17.57APCh. 17 - Give systematic names for the following structures...Ch. 17 - Give systematic names for the following structures...Ch. 17 - Prob. 17.60APCh. 17 - What compounds are produced from hydrolysis of...Ch. 17 - Procaine, a local anesthetic whose hydrochloride...Ch. 17 - Prob. 17.63APCh. 17 - Lactones are cyclic esters in which the carboxylic...Ch. 17 - When both the carboxylic acid and the amine are in...Ch. 17 - LSD (lysergic acid diethylamide), a semisynthetic...Ch. 17 - Prob. 17.67APCh. 17 - Prob. 17.68APCh. 17 - Prob. 17.69APCh. 17 - Prob. 17.70APCh. 17 - Prob. 17.71APCh. 17 - Prob. 17.72APCh. 17 - Prob. 17.73APCh. 17 - Prob. 17.74APCh. 17 - Prob. 17.75APCh. 17 - Three amide isomers, N,N-dimethylformamide,...Ch. 17 - Prob. 17.77CPCh. 17 - Prob. 17.78CPCh. 17 - Mention at least two simple chemical tests by...Ch. 17 - Prob. 17.80CPCh. 17 - Name the following compounds.Ch. 17 - Each of the following materials has an ester that...Ch. 17 - Prob. 17.83GPCh. 17 - Prob. 17.84GP
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