Practice Problems for Organic Chemistry by John McMurry

Studying organic chemistry with McMurry? The table below maps every chapter of the 10th (OpenStax) edition (OpenStax, 2023) to matching free practice on RealOChem — interactive problems with instant feedback, plus reaction worksheets curated from the chemical literature.

Free OpenStax edition.

Ch	Chapter	Matching practice on RealOChem
1	Structure and Bonding	Lewis Structures Molecular Geometry (VSEPR) Determine a Molecular Formula
2	Polar Covalent Bonds; Acids and Bases	Compare Resonance Contributors Resonance Arrows Resonance Formal Charges pKa Comparison (DMSO) pKa Comparison (Water) Find the Acidic Proton
3	Organic Compounds: Alkanes and Their Stereochemistry	Functional Group Identification Functional Group Classification IUPAC Nomenclature Nomenclingo (IUPAC Name Builder) Guided IUPAC Naming Newman Projections: Identify Newman Projections: Build Newman Projections: Rotate
4	Organic Compounds: Cycloalkanes and Their Stereochemistry	Chair Conformations: Ring Flip Chair Conformations: Energy
5	Stereochemistry at Tetrahedral Centers	Assign R or S Stereochemistry Identify meso Compounds Stereoisomer Relationships Molecule Relationships
6	An Overview of Organic Reactions	Mechanism Arrows
7	Alkenes: Structure and Reactivity	Assign E or Z Stereochemistry Electrophilic Addition to Alkenes/Alkynes — literature worksheet: problems / answer key
8	Alkenes: Reactions and Synthesis	Electrophilic Addition to Alkenes/Alkynes — literature worksheet: problems / answer key
9	Alkynes: An Introduction to Organic Synthesis	Electrophilic Addition to Alkenes/Alkynes — literature worksheet: problems / answer key
10	Organohalides	Radical Reactions — literature worksheet: problems / answer key
11	Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations	SN1/SN2/E1/E2 Prediction SN1 and SN2 Reactions — literature worksheet: problems / answer key E1 and E2 Reactions — literature worksheet: problems / answer key
12	Structure Determination: Mass Spectrometry and Infrared Spectroscopy	No practice for this chapter yet
13	Structure Determination: Nuclear Magnetic Resonance Spectroscopy	No practice for this chapter yet
14	Conjugated Compounds and Ultraviolet Spectroscopy	Diels-Alder Reactions — literature worksheet: problems / answer key
15	Benzene and Aromaticity	Identify Aromaticity
16	Chemistry of Benzene: Electrophilic Aromatic Substitution	Electrophilic Aromatic Substitution — literature worksheet: problems / answer key Nucleophilic Aromatic Substitution — literature worksheet: problems / answer key
17	Alcohols and Phenols	No practice for this chapter yet
18	Ethers and Epoxides; Thiols and Sulfides	No practice for this chapter yet
19	Aldehydes and Ketones: Nucleophilic Addition Reactions	Addition to Carbonyls — literature worksheet: problems / answer key Olefinations — literature worksheet: problems / answer key
20	Carboxylic Acids and Nitriles	No practice for this chapter yet
21	Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions	Substitution at Carbonyls — literature worksheet: problems / answer key
22	Carbonyl Alpha-Substitution Reactions	Keto-Enol Tautomerization — literature worksheet: problems Enolate Formation — literature worksheet: problems / answer key Enolate Alkylation — literature worksheet: problems / answer key Alpha Halogenation — literature worksheet: problems / answer key
23	Carbonyl Condensation Reactions	Aldol Reactions — literature worksheet: problems / answer key Claisen Condensations — literature worksheet: problems / answer key Complex Enolate Reactions — literature worksheet: problems / answer key
24	Amines and Heterocycles	No practice for this chapter yet
25	Biomolecules: Carbohydrates	No practice for this chapter yet
26	Biomolecules: Amino Acids, Peptides, and Proteins	No practice for this chapter yet
27	Biomolecules: Lipids	No practice for this chapter yet
28	Biomolecules: Nucleic Acids	No practice for this chapter yet
29	The Organic Chemistry of Metabolic Pathways	No practice for this chapter yet
30	Orbitals and Organic Chemistry: Pericyclic Reactions	Other Pericyclic Reactions — literature worksheet: problems / answer key
31	Synthetic Polymers	No practice for this chapter yet

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