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Introductory Chemistry - 1st Canadian Edition: Yields

Introductory Chemistry - 1st Canadian Edition
Yields
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table of contents
  1. Cover
  2. Title Page
  3. Copyright
  4. Table Of Contents
  5. Acknowledgments
  6. Dedication
  7. About BCcampus Open Education
  8. Chapter 1. What is Chemistry
    1. Some Basic Definitions
    2. Chemistry as a Science
  9. Chapter 2. Measurements
    1. Expressing Numbers
    2. Significant Figures
    3. Converting Units
    4. Other Units: Temperature and Density
    5. Expressing Units
    6. End-of-Chapter Material
  10. Chapter 3. Atoms, Molecules, and Ions
    1. Acids
    2. Ions and Ionic Compounds
    3. Masses of Atoms and Molecules
    4. Molecules and Chemical Nomenclature
    5. Atomic Theory
    6. End-of-Chapter Material
  11. Chapter 4. Chemical Reactions and Equations
    1. The Chemical Equation
    2. Types of Chemical Reactions: Single- and Double-Displacement Reactions
    3. Ionic Equations: A Closer Look
    4. Composition, Decomposition, and Combustion Reactions
    5. Oxidation-Reduction Reactions
    6. Neutralization Reactions
    7. End-of-Chapter Material
  12. Chapter 5. Stoichiometry and the Mole
    1. Stoichiometry
    2. The Mole
    3. Mole-Mass and Mass-Mass Calculations
    4. Limiting Reagents
    5. The Mole in Chemical Reactions
    6. Yields
    7. End-of-Chapter Material
  13. Chapter 6. Gases
    1. Pressure
    2. Gas Laws
    3. Other Gas Laws
    4. The Ideal Gas Law and Some Applications
    5. Gas Mixtures
    6. Kinetic Molecular Theory of Gases
    7. Molecular Effusion and Diffusion
    8. Real Gases
    9. End-of-Chapter Material
  14. Chapter 7. Energy and Chemistry
    1. Formation Reactions
    2. Energy
    3. Stoichiometry Calculations Using Enthalpy
    4. Enthalpy and Chemical Reactions
    5. Work and Heat
    6. Hess’s Law
    7. End-of-Chapter Material
  15. Chapter 8. Electronic Structure
    1. Light
    2. Quantum Numbers for Electrons
    3. Organization of Electrons in Atoms
    4. Electronic Structure and the Periodic Table
    5. Periodic Trends
    6. End-of-Chapter Material
  16. Chapter 9. Chemical Bonds
    1. Lewis Electron Dot Diagrams
    2. Electron Transfer: Ionic Bonds
    3. Covalent Bonds
    4. Other Aspects of Covalent Bonds
    5. Violations of the Octet Rule
    6. Molecular Shapes and Polarity
    7. Valence Bond Theory and Hybrid Orbitals
    8. Molecular Orbitals
    9. End-of-Chapter Material
  17. Chapter 10. Solids and Liquids
    1. Properties of Liquids
    2. Solids
    3. Phase Transitions: Melting, Boiling, and Subliming
    4. Intermolecular Forces
    5. End-of-Chapter Material
  18. Chapter 11. Solutions
    1. Colligative Properties of Solutions
    2. Concentrations as Conversion Factors
    3. Quantitative Units of Concentration
    4. Colligative Properties of Ionic Solutes
    5. Some Definitions
    6. Dilutions and Concentrations
    7. End-of-Chapter Material
  19. Chapter 12. Acids and Bases
    1. Acid-Base Titrations
    2. Strong and Weak Acids and Bases and Their Salts
    3. Brønsted-Lowry Acids and Bases
    4. Arrhenius Acids and Bases
    5. Autoionization of Water
    6. Buffers
    7. The pH Scale
    8. End-of-Chapter Material
  20. Chapter 13. Chemical Equilibrium
    1. Chemical Equilibrium
    2. The Equilibrium Constant
    3. Shifting Equilibria: Le Chatelier’s Principle
    4. Calculating Equilibrium Constant Values
    5. Some Special Types of Equilibria
    6. End-of-Chapter Material
  21. Chapter 14. Oxidation and Reduction
    1. Oxidation-Reduction Reactions
    2. Balancing Redox Reactions
    3. Applications of Redox Reactions: Voltaic Cells
    4. Electrolysis
    5. End-of-Chapter Material
  22. Chapter 15. Nuclear Chemistry
    1. Units of Radioactivity
    2. Uses of Radioactive Isotopes
    3. Half-Life
    4. Radioactivity
    5. Nuclear Energy
    6. End-of-Chapter Material
  23. Chapter 16. Organic Chemistry
    1. Hydrocarbons
    2. Branched Hydrocarbons
    3. Alkyl Halides and Alcohols
    4. Other Oxygen-Containing Functional Groups
    5. Other Functional Groups
    6. Polymers
    7. End-of-Chapter Material
  24. Chapter 17. Kinetics
    1. Factors that Affect the Rate of Reactions
    2. Reaction Rates
    3. Rate Laws
    4. Concentration–Time Relationships: Integrated Rate Laws
    5. Activation Energy and the Arrhenius Equation
    6. Reaction Mechanisms
    7. Catalysis
    8. End-of-Chapter Material
  25. Chapter 18. Chemical Thermodynamics
    1. Spontaneous Change
    2. Entropy and the Second Law of Thermodynamics
    3. Measuring Entropy and Entropy Changes
    4. Gibbs Free Energy
    5. Spontaneity: Free Energy and Temperature
    6. Free Energy under Nonstandard Conditions
    7. End-of-Chapter Material
  26. Appendix A: Periodic Table of the Elements
  27. Appendix B: Selected Acid Dissociation Constants at 25°C
  28. Appendix C: Solubility Constants for Compounds at 25°C
  29. Appendix D: Standard Thermodynamic Quantities for Chemical Substances at 25°C
  30. Appendix E: Standard Reduction Potentials by Value
  31. Glossary
  32. About the Authors
  33. Versioning History

Yields

Learning Objectives

  1. Define and determine theoretical yields, actual yields, and percent yields.

In all the previous calculations we have performed involving balanced chemical equations, we made two assumptions:

  1. The reaction goes exactly as written.
  2. The reaction proceeds completely.

In reality, such things as side reactions occur that make some chemical reactions rather messy. For example, in the actual combustion of some carbon-containing compounds, such as methane, some CO is produced as well as CO2. However, we will continue to ignore side reactions, unless otherwise noted.

The second assumption, that the reaction proceeds completely, is more troublesome. Many chemical reactions do not proceed to completion as written, for a variety of reasons (some of which we will consider in Chapter 13 “Chemical Equilibrium”). When we calculate an amount of product assuming that all the reactant reacts, we calculate the theoretical yield, an amount that is theoretically produced as calculated using the balanced chemical reaction.

In many cases, however, this is not what really happens. In many cases, less—sometimes much less—of a product is made during the course of a chemical reaction. The amount that is actually produced in a reaction is called the actual yield. By definition, the actual yield is less than or equal to the theoretical yield. If it is not, then an error has been made.

Both theoretical yields and actual yields are expressed in units of moles or grams. It is also common to see something called a percent yield. The percent yield is a comparison between the actual yield and the theoretical yield and is defined as:

\text{percent yield}=\dfrac{\text{actual yield}}{\text{theoretical yield}}\times 100\%

It does not matter whether the actual and theoretical yields are expressed in moles or grams, as long as they are expressed in the same units. However, the percent yield always has units of percent. Proper percent yields are between 0% and 100%—again, if percent yield is greater than 100%, an error has been made.

Example 5.14

Problem

A worker reacts 30.5 g of Zn with nitric acid and evaporates the remaining water to obtain 65.2 g of Zn(NO3)2. What are the theoretical yield, the actual yield, and the percent yield?

Zn(s) + 2HNO3(aq) → Zn(NO3)2(aq) + H2(g)

Solution

A mass-mass calculation can be performed to determine the theoretical yield. We need the molar masses of Zn (65.39 g/mol) and Zn(NO3)2 (189.41 g/mol). In three steps, the mass-mass calculation is:

30.5\text{ \cancel{g Zn}}\times \dfrac{1\text{ \cancel{mol Zn}}}{65.39\text{ \cancel{g Zn}}}\times \dfrac{1\cancel{\text{ mol }\ce{Zn(NO3)2}}}{1\text{ \cancel{mol Zn}}}\times \dfrac{189.41\text{ g }\ce{Zn(NO3)2}}{1\cancel{\text{ mol }\ce{Zn(NO3)2}}}=88.3\text{ g }\ce{Zn(NO3)2}

Thus, the theoretical yield is 88.3 g of Zn(NO3)2. The actual yield is the amount that was actually made, which was 65.2 g of Zn(NO3)2. To calculate the percent yield, we take the actual yield and divide it by the theoretical yield and multiply by 100:

\dfrac{65.2\text{ g }\ce{Zn(NO3)2}}{88.3\text{ }\ce{Zn(NO3)2}}\times 100\% = 73.8\%

The worker achieved almost three-fourths of the possible yield.

Test Yourself

A synthesis produced 2.05 g of NH3 from 16.5 g of N2. What is the theoretical yield and the percent yield?

N2(g) + 3H2(g) → 2NH3(g)

Answer

theoretical yield = 20.1 g; percent yield = 10.2%

Chemistry Is Everywhere: Actual Yields in Drug Synthesis and Purification

Many drugs are the product of several steps of chemical synthesis. Each step typically occurs with less than 100% yield, so the overall percent yield might be very small. The general rule is that the overall percent yield is the product of the percent yields of the individual synthesis steps. For a drug synthesis that has many steps, the overall percent yield can be very tiny, which is one factor in the huge cost of some drugs. For example, if a 10-step synthesis has a percent yield of 90% for each step, the overall yield for the entire synthesis is only 35%. Many scientists work every day trying to improve percent yields of the steps in the synthesis to decrease costs, improve profits, and minimize waste.

Even purifications of complex molecules into drug-quality purity are subject to percent yields. Consider the purification of impure albuterol. Albuterol (C13H21NO2; accompanying figure) is an inhaled drug used to treat asthma, bronchitis, and other obstructive pulmonary diseases. It is synthesized from norepinephrine, a naturally occurring hormone and neurotransmitter. Its initial synthesis makes very impure albuterol that is purified in five chemical steps. The details of the steps do not concern us; only the percent yields do.

Table 5.1 Percent yield of the purification of albuterol
SynthesisPercent Yield
impure albuterol → intermediate A70%
intermediate A → intermediate B100%
intermediate B → intermediate C40%
intermediate C → intermediate D72%
intermediate D → purified albuterol35%
impure albuterol → purified albuterol70% × 100% × 40% × 72% × 35% = 7.5%

That is, only about one-fourteenth of the original material was turned into the purified drug. This gives you one reason why some drugs are so expensive; a lot of material is lost in making a high-purity pharmaceutical.

Key Takeaways

  • Theoretical yield is what you calculate the yield will be using the balanced chemical reaction.
  • Actual yield is what you actually get in a chemical reaction.
  • Percent yield is a comparison of the actual yield with the theoretical yield.

Exercises

Questions

  1. What is the difference between the theoretical yield and the actual yield?
  2. What is the difference between the actual yield and the percent yield?
  3. A worker isolates 2.675 g of SiF4 after reacting 2.339 g of SiO2 with HF. What are the theoretical yield and the actual yield?

    SiO2(s) + 4HF(g) → SiF4(g) + 2H2O(ℓ)

  4. A worker synthesizes aspirin, C9H8O4, according to this chemical equation. If 12.66 g of C7H6O3 are reacted and 12.03 g of aspirin are isolated, what are the theoretical yield and the actual yield?

    C7H6O3 + C4H6O3 → C9H8O4 + HC2H3O2

  5. A chemist decomposes 1.006 g of NaHCO3 and obtains 0.0334 g of Na2CO3. What are the theoretical yield and the actual yield?

    2NaHCO3(s) → Na2CO3(s) + H2O(ℓ) + CO2(g)

  6. A chemist combusts a 3.009 g sample of C5H12 and obtains 3.774 g of H2O. What are the theoretical yield and the actual yield?

    C5H12(ℓ) + 8 O2(g) → 5CO2 + 6H2O(ℓ)

  7. What is the percent yield in Exercise 3?
  8. What is the percent yield in Exercise 4?
  9. What is the percent yield in Exercise 5?
  10. What is the percent yield in Exercise 6?

Answers

  1. Theoretical yield is what you expect stoichiometrically from a chemical reaction; actual yield is what you actually get from a chemical reaction.
  1. theoretical yield = 4.052 g; actual yield = 2.675 g
  1. theoretical yield = 0.635 g; actual yield = 0.0334 g
  1. 66.02%
  1. 5.26%

Annotate

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Copyright © 2014

                                by Jessie A. Key

            Introductory Chemistry - 1st Canadian Edition by Jessie A. Key is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License, except where otherwise noted.
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