Organic Chemistry 5th Edition, Student Study Guide and Solutions – (Klein & Starkey, 2025) | All 27 Chapters Covered

Covers All 27 Chapters

, CONTENTS

Chapter 1 – Electrons, Bonds, and Molecular Properties 1
Chapter 2 – Molecular Representations 27
Chapter 3 – Acids and Bases 69
Chapter 4 – Alkanes and Cycloalkanes 110
Chapter 5 – Stereoisomerism 141
Chapter 6 – Chemical Reactivity and Mechanisms 173
Chapter 7 – Alkyl Halides: Nucleophilic Substitution and Elimination Reactions 195
Chapter 8 – Addition Reactions of Alkenes 262
Chapter 9 – Alkynes 317
Chapter 10 – Radical Reactions 368
Chapter 11 – Synthesis 409
Chapter 12 – Alcohols and Phenols 449
Chapter 13 – Ethers and Epoxides; Thiols and Sulfides 510
Chapter 14 – Infrared Spectroscopy and Mass Spectrometry 563
Chapter 15 – Nuclear Magnetic Resonance Spectroscopy 593
Chapter 16 – Conjugated Pi Systems and Pericyclic Reactions 639
Chapter 17 – Aromatic Compounds 682
Chapter 18 – Aromatic Substitution Reactions 717
Chapter 19 – Aldehydes and Ketones 790
Chapter 20 – Carboxylic Acids and Their Derivatives 865
Chapter 21 – Alpha Carbon Chemistry: Enols and Enolates 929
Chapter 22 – Amines 1010
Chapter 23 – Introduction to Organometallic Compounds 1071
Chapter 24 – Carbohydrates 1126
Chapter 25 – Amino Acids, Peptides, and Proteins 1154
Chapter 26 – Lipids 1183
Chapter 27 – Synthetic Polymers 1202

, Chapter 1
A Review of General Chemistry:
Electrons, Bonds and Molecular Properties
Review of Concepts
Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of
Chapter 1. Each of the sentences below appears verbatim in the section entitled Review of Concepts and
Vocabulary.

 _____________ isomers share the same molecular formula but have different connectivity of
atoms and different physical properties.
 Second-row elements generally obey the _______ rule, bonding to achieve noble gas electron
configuration.
 A pair of unshared electrons is called a ______________.
 A formal charge occurs when atoms do not exhibit the appropriate number of
___________________________.
 An atomic orbital is a region of space associated with ____________________, while a
molecular orbital is associated with _______________________.
 Methane’s tetrahedral geometry can be explained using four degenerate _____-hybridized
orbitals to achieve its four single bonds.
 Ethylene’s planar geometry can be explained using three degenerate _____-hybridized orbitals.
 Acetylene’s linear geometry is achieved via _____-hybridized carbon atoms.
 The geometry of small compounds can be predicted using valence shell electron pair repulsion
(VSEPR) theory, which focuses on the number of  bonds and _______________
exhibited by each atom.
 The physical properties of compounds are determined by __________________ forces, the
attractive forces between molecules.
 London dispersion forces result from the interaction between transient __________________
and are stronger for larger alkanes due to their larger surface area and ability to accommodate
more interactions.

Review of Skills
Fill in the blanks and empty boxes below. To verify that your answers are correct, look in your textbook at
the end of Chapter 1. The answers appear in the section entitled SkillBuilder Review.
SkillBuilder 1.1 Drawing Constitutional Isomers of Small Molecules




SkillBuilder 1.2 Drawing the Lewis Structure of a Small Molecule

, 2 CHAPTER 1


SkillBuilder 1.3 Calculating Formal Charge




SkillBuilder 1.4 Locating Partial Charges Resulting from Induction




SkillBuilder 1.5 Reading Bond-Line Structures




SkillBuilder 1.6 Identifying Electron Configurations
Step 1 In the energy Step 2 Fill in the boxes below with the
diagram shown here, 2p numbers that correctly describe the
draw the electron electron configuration of nitrogen.
configuration of nitrogen 2s
(using arrows to
represent electrons). 1s 1s 2s 2p
Nitrogen

SkillBuilder 1.7 Identifying Hybridization States