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Organic Chemistry I

(4 reviews)

organic chemistry homework

Xin Liu, Kwantlen Polytechnic University

Copyright Year: 2021

ISBN 13: 9781989864524

Publisher: Kwantlen Polytechnic University

Language: English

Formats Available

Conditions of use.

Attribution-NonCommercial-ShareAlike

Learn more about reviews.

Reviewed by Ratanmani Joshi, Professor, Tidewater Community College on 2/23/23

The text covers most areas and ideas of the subject and does provide good glossary. read more

Comprehensiveness rating: 5 see less

The text covers most areas and ideas of the subject and does provide good glossary.

Content Accuracy rating: 5

There are very few errors, but overall it is accurate and unbiased.

Relevance/Longevity rating: 5

The book is quite relevant, since it covers most basic concepts of Organic chemistry I for freshman and sophomore students.

Clarity rating: 4

Book content is very clear, but some more example could have been included for practice purpose.

Consistency rating: 5

All terminologies mentioned in the test are very well explained.

Modularity rating: 5

I really like the way sections are broken for each chapter.

Organization/Structure/Flow rating: 4

Book organization/ structure/flow are good except certain topics are omitted out. For example in the spectroscopy chapter, the author should have included introduction of mass spectroscopy also along with IR and NMR.

Interface rating: 5

No interface issues.

Grammatical Errors rating: 5

Few grammatical error but overall concepts can be understood.

Cultural Relevance rating: 5

No cultural relevance in the book.

Overall the book is really good a an OER option. Covers major concepts of Organic Chemistry I for students. However more practice problems could be included with each chapter.

Reviewed by Hermann Christine, Chair, Full Professor, Radford University on 1/10/23

This textbook covers most topics in the first semester of the year-long Organic Chemistry sequence. More examples of IR and NMR interpretation and nomenclature examples are needed. Many topics are not covered in much detail such as nomenclature... read more

Comprehensiveness rating: 3 see less

This textbook covers most topics in the first semester of the year-long Organic Chemistry sequence. More examples of IR and NMR interpretation and nomenclature examples are needed. Many topics are not covered in much detail such as nomenclature and VSEPR. An index, glossary, and many end of chapter problems would be useful.

The material that is presented is accurate.

Relevance/Longevity rating: 4

Real world examples would improve the textbook, as students want to know how this relates to their real life. The topics that are included are the basics of organic chemistry.

The text is written so that it is easy to understand. However, the numerous typos distract from the text. The examples that are present are illustrated well. However, many more examples and problems are needed.

The textbook is consistent throughout in style. Color pictures explain topics well.

The headings and sub-headings are excellent. Many more examples are needed for students. All students need many examples to understand the topic.

Organization/Structure/Flow rating: 5

The topics are presented in a logical manner. However, more examples are needed to explain the concepts.

The images are clear and easy to read. Table of contents is easy to follow.

Grammatical Errors rating: 3

Numerous typos are in the textbook. For example, carbocation is labelled carocation

The chemistry topics are listed typical for an organic book. These are facts and not related to culture.

It is a basic organic book for the first semester of Organic Chemistry. However, it does not give enough explanation or examples for many topics.

Reviewed by SATHIAMOORTHY BALASUBRAMANIAN, Chemistry FACULTY, Rochester Community & Technical College on 12/11/22

This text book covers all the chapters required for 1st semester of Organic chemistry course. It is comprehensive yet precise in outlining the various concepts involved. read more

This text book covers all the chapters required for 1st semester of Organic chemistry course. It is comprehensive yet precise in outlining the various concepts involved.

Content Accuracy rating: 4

Appears accurate and error free on basic reading.

This text book is highly relevant for understanding the fundamentals of Organic chemistry course. The various concepts are well organized and explained in detail. This book can be used by a student to self teach the principles in Organic chemistry.

Clarity rating: 5

This text book is easy to understand and is supplemented by excellent examples. I would specially highlight the various examples given in the text book as they are the tools which lead to clear understanding.

Is consistent throughout

The author has well thought out the various sections in the text book. One can use any of these sections in providing assignments to students.

Well organized and easy to understand. It has a connect from one concept to another likewise from one chapter to another.

There aren't any interface issues.

There are grammatical errors in tense used but it shouldn't be an issue in understanding the concepts being dealt in the book.

Cultural Relevance rating: 1

Not applicable

A well written organic chemistry text book for Freshman and sophomore students. Some grammatical errors need to be corrected but that doesn't cause issues in understanding the concepts being dealt. I would surely recommend students to utilize the examples and questions given in this book for further practice and better understanding of principles of Organic Chemistry

Reviewed by Maggie Bump, Senior Instructor, Virginia Tech on 5/23/22

This text covers half of the standard undergraduate Organic Chemistry concepts and reactions and is reasonable coverage for one semester of the course. The text does not address polymers, pharmaceuticals, biomaterials, or green chemistry. These... read more

Comprehensiveness rating: 4 see less

This text covers half of the standard undergraduate Organic Chemistry concepts and reactions and is reasonable coverage for one semester of the course. The text does not address polymers, pharmaceuticals, biomaterials, or green chemistry. These evolving areas will need to be incorporated by the professor. Inclusion of an index, glossary, and summary of reactions would be a great addition.

Content is accurate and unbiased.

The material included is up-to-date coverage of longstanding principles and reactions, content that does not change quickly. Real-world applications, such as vinyl polymerizations used on a large industrial scale, are not included but would improve the relevance of the text material.

The text is written at a level appropriate for freshmen and sophomore Organic Chemistry students. Examples and Common Error boxes are useful and well placed. The grammatical errors are distracting and may cause minor issues for some learning styles.

The text throughout the chapters is consistent in style and in level of both content and presentation of the content.

Chapters and subheadings are used effectively to make the text divisible into pre- and post- class readings, or for adapting the order of the material for customized coverage.

The topics are presented in a logical order and clear fashion.

The text is free of significant interface issues. Images appear clear and navigating between the table of contents and embedded links is logical and smooth.

There are several small grammatical errors, mainly verb tense and noun pluralization. These are distracting, but not inhibitory to understanding the content.

The chemistry is presented in a scientific manner. There are not statements of opinion, and there are not examples that are culturally insensitive.

For a new teacher of the subject, challenges include limited practice problems, no test questions, and no ‘fun facts’ showing real world examples. I am going to offer this text as a resource in my class this fall because it is well organized and written at an appropriate level, but I have been teaching the course for 20 years. I have developed resources for my classes, so having only this text is a fine fit for my class. I will use my notes, practice problems, homework sheets, and examples with this text.

Table of Contents

  • Chapter 1 Basic Concepts in Chemical Bonding and Organic Molecules
  • Chapter 2 Fundamental of Organic Structures
  • Chapter 3 Acids and Bases: Organic Reaction Mechanism Introduction
  • Chapter 4 Conformations of Alkanes and Cycloalkanes
  • Chapter 5 Stereochemistry
  • Chapter 6 Structural Identification of Organic Compounds: IR and NMR Spectroscopy
  • Chapter 7 Nucleophilic Substitution Reactions
  • Chapter 8 Elimination Reactions
  • Chapter 9 Free Radical Substitution Reaction of Alkanes
  • Chapter 10 Alkenes and Alkynes

Ancillary Material

About the book.

An open textbook that is suitable for the first semester of Organic Chemistry. Basic concepts of the structures and reactivities of organic molecules are covered in this open textbook. Besides the fundamental discussions of organic acids-bases, stereochemistry, IR and NMR, this book also includes the topics of substitution and elimination reactions, radical substitution of alkanes, preparation and reactions of alkenes and alkynes.

About the Contributors

Dr. Xin Liu has been a faculty member at the Department of Chemistry, KPU since 2008. Other than teaching Organic Chemistry and first-year General Chemistry courses, she has also been actively involved in curriculum review and new course development. Having a keen interest in Open Education Resource,  Dr. Liu hope to make more contributions in this fast growing area, to make learning accessible to everyone.

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Over 400+ blog posts to guide you through introductory Organic Chemistry, organized by subject.

00 General Chemistry Review

  • Lewis Structures
  • Ionic and Covalent Bonding
  • Chemical Kinetics
  • Chemical Equilibria
  • Valence Electrons of the First Row Elements
  • How Concepts Build Up In Org 1 ("The Pyramid")

01 Bonding, Structure, and Resonance

  • How Do We Know Methane (CH4) Is Tetrahedral?
  • Hybrid Orbitals and Hybridization
  • How To Determine Hybridization: A Shortcut
  • Orbital Hybridization And Bond Strengths
  • Sigma bonds come in six varieties: Pi bonds come in one
  • A Key Skill: How to Calculate Formal Charge
  • The Four Intermolecular Forces and How They Affect Boiling Points
  • 3 Trends That Affect Boiling Points
  • How To Use Electronegativity To Determine Electron Density (and why NOT to trust formal charge)
  • Introduction to Resonance
  • How To Use Curved Arrows To Interchange Resonance Forms
  • Evaluating Resonance Forms (1) - The Rule of Least Charges
  • How To Find The Best Resonance Structure By Applying Electronegativity
  • Evaluating Resonance Structures With Negative Charges
  • Evaluating Resonance Structures With Positive Charge
  • Exploring Resonance: Pi-Donation
  • Exploring Resonance: Pi-acceptors
  • In Summary: Evaluating Resonance Structures
  • Drawing Resonance Structures: 3 Common Mistakes To Avoid
  • How to apply electronegativity and resonance to understand reactivity
  • Bond Hybridization Practice
  • Structure and Bonding Practice Quizzes
  • Resonance Structures Practice

02 Acid Base Reactions

  • Introduction to Acid-Base Reactions
  • Acid Base Reactions In Organic Chemistry
  • The Stronger The Acid, The Weaker The Conjugate Base
  • Walkthrough of Acid-Base Reactions (3) - Acidity Trends
  • Five Key Factors That Influence Acidity
  • Acid-Base Reactions: Introducing Ka and pKa
  • How to Use a pKa Table
  • The pKa Table Is Your Friend
  • A Handy Rule of Thumb for Acid-Base Reactions
  • Acid Base Reactions Are Fast
  • pKa Values Span 60 Orders Of Magnitude
  • How Protonation and Deprotonation Affect Reactivity
  • Acid Base Practice Problems

03 Alkanes and Nomenclature

  • Meet the (Most Important) Functional Groups
  • Condensed Formulas: Deciphering What the Brackets Mean
  • Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions
  • Don't Be Futyl, Learn The Butyls
  • Primary, Secondary, Tertiary, Quaternary In Organic Chemistry
  • Branching, and Its Affect On Melting and Boiling Points
  • The Many, Many Ways of Drawing Butane
  • Wedge And Dash Convention For Tetrahedral Carbon
  • Common Mistakes in Organic Chemistry: Pentavalent Carbon
  • Table of Functional Group Priorities for Nomenclature
  • Summary Sheet - Alkane Nomenclature
  • Organic Chemistry IUPAC Nomenclature Demystified With A Simple Puzzle Piece Approach
  • Boiling Point Quizzes
  • Organic Chemistry Nomenclature Quizzes

04 Conformations and Cycloalkanes

  • Staggered vs Eclipsed Conformations of Ethane
  • Conformational Isomers of Propane
  • Newman Projection of Butane (and Gauche Conformation)
  • Introduction to Cycloalkanes (1)
  • Geometric Isomers In Small Rings: Cis And Trans Cycloalkanes
  • Calculation of Ring Strain In Cycloalkanes
  • Cycloalkanes - Ring Strain In Cyclopropane And Cyclobutane
  • Cyclohexane Conformations
  • Cyclohexane Chair Conformation: An Aerial Tour
  • How To Draw The Cyclohexane Chair Conformation
  • The Cyclohexane Chair Flip
  • The Cyclohexane Chair Flip - Energy Diagram
  • Substituted Cyclohexanes - Axial vs Equatorial
  • Ranking The Bulkiness Of Substituents On Cyclohexanes: "A-Values"
  • Cyclohexane Chair Conformation Stability: Which One Is Lower Energy?
  • Fused Rings - Cis-Decalin and Trans-Decalin
  • Naming Bicyclic Compounds - Fused, Bridged, and Spiro
  • Bredt's Rule (And Summary of Cycloalkanes)
  • Newman Projection Practice
  • Cycloalkanes Practice Problems

05 A Primer On Organic Reactions

  • The Most Important Question To Ask When Learning a New Reaction
  • Learning New Reactions: How Do The Electrons Move?
  • The Third Most Important Question to Ask When Learning A New Reaction
  • 7 Factors that stabilize negative charge in organic chemistry
  • 7 Factors That Stabilize Positive Charge in Organic Chemistry
  • Nucleophiles and Electrophiles
  • Curved Arrows (for reactions)
  • Curved Arrows (2): Initial Tails and Final Heads
  • Nucleophilicity vs. Basicity
  • The Three Classes of Nucleophiles
  • What Makes A Good Nucleophile?
  • What makes a good leaving group?
  • 3 Factors That Stabilize Carbocations
  • Equilibrium and Energy Relationships
  • What's a Transition State?
  • Hammond's Postulate
  • Learning Organic Chemistry Reactions: A Checklist (PDF)
  • Introduction to Free Radical Substitution Reactions
  • Introduction to Oxidative Cleavage Reactions

06 Free Radical Reactions

  • Bond Dissociation Energies = Homolytic Cleavage
  • Free Radical Reactions
  • 3 Factors That Stabilize Free Radicals
  • What Factors Destabilize Free Radicals?
  • Bond Strengths And Radical Stability
  • Free Radical Initiation: Why Is "Light" Or "Heat" Required?
  • Initiation, Propagation, Termination
  • Monochlorination Products Of Propane, Pentane, And Other Alkanes
  • Selectivity In Free Radical Reactions
  • Selectivity in Free Radical Reactions: Bromination vs. Chlorination
  • Halogenation At Tiffany's
  • Allylic Bromination
  • Bonus Topic: Allylic Rearrangements
  • In Summary: Free Radicals
  • Synthesis (2) - Reactions of Alkanes
  • Free Radicals Practice Quizzes

07 Stereochemistry and Chirality

  • Types of Isomers: Constitutional Isomers, Stereoisomers, Enantiomers, and Diastereomers
  • How To Draw The Enantiomer Of A Chiral Molecule
  • How To Draw A Bond Rotation
  • Introduction to Assigning (R) and (S): The Cahn-Ingold-Prelog Rules
  • Assigning Cahn-Ingold-Prelog (CIP) Priorities (2) - The Method of Dots
  • Enantiomers vs Diastereomers vs The Same? Two Methods For Solving Problems
  • Assigning R/S To Newman Projections (And Converting Newman To Line Diagrams)
  • How To Determine R and S Configurations On A Fischer Projection
  • The Meso Trap
  • Optical Rotation, Optical Activity, and Specific Rotation
  • Optical Purity and Enantiomeric Excess
  • What's a Racemic Mixture?
  • Chiral Allenes And Chiral Axes
  • Stereochemistry Practice Problems and Quizzes

08 Substitution Reactions

  • Introduction to Nucleophilic Substitution Reactions
  • Walkthrough of Substitution Reactions (1) - Introduction
  • Two Types of Nucleophilic Substitution Reactions
  • The SN2 Mechanism
  • Why the SN2 Reaction Is Powerful
  • The SN1 Mechanism
  • The Conjugate Acid Is A Better Leaving Group
  • Comparing the SN1 and SN2 Reactions
  • Polar Protic? Polar Aprotic? Nonpolar? All About Solvents
  • Steric Hindrance is Like a Fat Goalie
  • Common Blind Spot: Intramolecular Reactions
  • The Conjugate Base is Always a Stronger Nucleophile
  • Substitution Practice - SN1
  • Substitution Practice - SN2

09 Elimination Reactions

  • Elimination Reactions (1): Introduction And The Key Pattern
  • Elimination Reactions (2): The Zaitsev Rule
  • Elimination Reactions Are Favored By Heat
  • Two Elimination Reaction Patterns
  • The E1 Reaction
  • The E2 Mechanism
  • E1 vs E2: Comparing the E1 and E2 Reactions
  • Antiperiplanar Relationships: The E2 Reaction and Cyclohexane Rings
  • Bulky Bases in Elimination Reactions
  • Comparing the E1 vs SN1 Reactions
  • Elimination (E1) Reactions With Rearrangements
  • E1cB - Elimination (Unimolecular) Conjugate Base
  • Elimination (E1) Practice Problems And Solutions
  • Elimination (E2) Practice Problems and Solutions

10 Rearrangements

  • Introduction to Rearrangement Reactions
  • Rearrangement Reactions (1) - Hydride Shifts
  • Carbocation Rearrangement Reactions (2) - Alkyl Shifts
  • Pinacol Rearrangement
  • The SN1, E1, and Alkene Addition Reactions All Pass Through A Carbocation Intermediate

11 SN1/SN2/E1/E2 Decision

  • Identifying Where Substitution and Elimination Reactions Happen
  • Deciding SN1/SN2/E1/E2 (1) - The Substrate
  • Deciding SN1/SN2/E1/E2 (2) - The Nucleophile/Base
  • SN1 vs E1 and SN2 vs E2 : The Temperature
  • Deciding SN1/SN2/E1/E2 - The Solvent
  • Wrapup: The Key Factors For Determining SN1/SN2/E1/E2
  • Alkyl Halide Reaction Map And Summary
  • SN1 SN2 E1 E2 Practice Problems

12 Alkene Reactions

  • E and Z Notation For Alkenes (+ Cis/Trans)
  • Alkene Stability
  • Alkene Addition Reactions: "Regioselectivity" and "Stereoselectivity" (Syn/Anti)
  • Stereoselective and Stereospecific Reactions
  • Hydrohalogenation of Alkenes and Markovnikov's Rule
  • Hydration of Alkenes With Aqueous Acid
  • Rearrangements in Alkene Addition Reactions
  • Halogenation of Alkenes and Halohydrin Formation
  • Oxymercuration Demercuration of Alkenes
  • Hydroboration Oxidation of Alkenes
  • m-CPBA (meta-chloroperoxybenzoic acid)
  • OsO4 (Osmium Tetroxide) for Dihydroxylation of Alkenes
  • Palladium on Carbon (Pd/C) for Catalytic Hydrogenation of Alkenes
  • Cyclopropanation of Alkenes
  • A Fourth Alkene Addition Pattern - Free Radical Addition
  • Alkene Reactions: Ozonolysis
  • Summary: Three Key Families Of Alkene Reaction Mechanisms
  • Synthesis (4) - Alkene Reaction Map, Including Alkyl Halide Reactions
  • Alkene Reactions Practice Problems

13 Alkyne Reactions

  • Acetylides from Alkynes, And Substitution Reactions of Acetylides
  • Partial Reduction of Alkynes With Lindlar's Catalyst
  • Partial Reduction of Alkynes With Na/NH3 To Obtain Trans Alkenes
  • Alkyne Hydroboration With "R2BH"
  • Hydration and Oxymercuration of Alkynes
  • Hydrohalogenation of Alkynes
  • Alkyne Halogenation: Bromination, Chlorination, and Iodination of Alkynes
  • Alkyne Reactions - The "Concerted" Pathway
  • Alkenes To Alkynes Via Halogenation And Elimination Reactions
  • Alkynes Are A Blank Canvas
  • Synthesis (5) - Reactions of Alkynes
  • Alkyne Reactions Practice Problems With Answers

14 Alcohols, Epoxides and Ethers

  • Alcohols - Nomenclature and Properties
  • Alcohols Can Act As Acids Or Bases (And Why It Matters)
  • Alcohols - Acidity and Basicity
  • The Williamson Ether Synthesis
  • Ethers From Alkenes, Tertiary Alkyl Halides and Alkoxymercuration
  • Alcohols To Ethers via Acid Catalysis
  • Cleavage Of Ethers With Acid
  • Epoxides - The Outlier Of The Ether Family
  • Opening of Epoxides With Acid
  • Epoxide Ring Opening With Base
  • Making Alkyl Halides From Alcohols
  • Tosylates And Mesylates
  • PBr3 and SOCl2
  • Elimination Reactions of Alcohols
  • Elimination of Alcohols To Alkenes With POCl3
  • Alcohol Oxidation: "Strong" and "Weak" Oxidants
  • Demystifying The Mechanisms of Alcohol Oxidations
  • Protecting Groups For Alcohols
  • Thiols And Thioethers
  • Calculating the oxidation state of a carbon
  • Oxidation and Reduction in Organic Chemistry
  • Oxidation Ladders
  • SOCl2 Mechanism For Alcohols To Alkyl Halides: SN2 versus SNi
  • Alcohol Reactions Roadmap (PDF)
  • Alcohol Reaction Practice Problems
  • Epoxide Reaction Quizzes
  • Oxidation and Reduction Practice Quizzes

15 Organometallics

  • What's An Organometallic?
  • Formation of Grignard and Organolithium Reagents
  • Organometallics Are Strong Bases
  • Reactions of Grignard Reagents
  • Protecting Groups In Grignard Reactions
  • Synthesis Problems Involving Grignard Reagents
  • Grignard Reactions And Synthesis (2)
  • Organocuprates (Gilman Reagents): How They're Made
  • Gilman Reagents (Organocuprates): What They're Used For
  • The Heck, Suzuki, and Olefin Metathesis Reactions (And Why They Don't Belong In Most Introductory Organic Chemistry Courses)
  • Reaction Map: Reactions of Organometallics
  • Grignard Practice Problems

16 Spectroscopy

  • Degrees of Unsaturation (or IHD, Index of Hydrogen Deficiency)
  • Conjugation And Color (+ How Bleach Works)
  • Introduction To UV-Vis Spectroscopy
  • UV-Vis Spectroscopy: Absorbance of Carbonyls
  • UV-Vis Spectroscopy: Practice Questions
  • Bond Vibrations, Infrared Spectroscopy, and the "Ball and Spring" Model
  • Infrared Spectroscopy: A Quick Primer On Interpreting Spectra
  • IR Spectroscopy: 4 Practice Problems
  • 1H NMR: How Many Signals?
  • Homotopic, Enantiotopic, Diastereotopic
  • Diastereotopic Protons in 1H NMR Spectroscopy: Examples
  • C13 NMR - How Many Signals
  • Liquid Gold: Pheromones In Doe Urine
  • Natural Product Isolation (1) - Extraction
  • Natural Product Isolation (2) - Purification Techniques, An Overview
  • Structure Determination Case Study: Deer Tarsal Gland Pheromone

17 Dienes and MO Theory

  • What To Expect In Organic Chemistry 2
  • Are these molecules conjugated?
  • Conjugation And Resonance In Organic Chemistry
  • Bonding And Antibonding Pi Orbitals
  • Molecular Orbitals of The Allyl Cation, Allyl Radical, and Allyl Anion
  • Pi Molecular Orbitals of Butadiene
  • Reactions of Dienes: 1,2 and 1,4 Addition
  • Thermodynamic and Kinetic Products
  • More On 1,2 and 1,4 Additions To Dienes
  • s-cis and s-trans
  • The Diels-Alder Reaction
  • Cyclic Dienes and Dienophiles in the Diels-Alder Reaction
  • Stereochemistry of the Diels-Alder Reaction
  • Exo vs Endo Products In The Diels Alder: How To Tell Them Apart
  • HOMO and LUMO In the Diels Alder Reaction
  • Why Are Endo vs Exo Products Favored in the Diels-Alder Reaction?
  • Diels-Alder Reaction: Kinetic and Thermodynamic Control
  • The Retro Diels-Alder Reaction
  • The Intramolecular Diels Alder Reaction
  • Regiochemistry In The Diels-Alder Reaction
  • The Cope and Claisen Rearrangements
  • Electrocyclic Reactions
  • Electrocyclic Ring Opening And Closure (2) - Six (or Eight) Pi Electrons
  • Diels Alder Practice Problems
  • Molecular Orbital Theory Practice

18 Aromaticity

  • Introduction To Aromaticity
  • Rules For Aromaticity
  • Huckel's Rule: What Does 4n+2 Mean?
  • Aromatic, Non-Aromatic, or Antiaromatic? Some Practice Problems
  • Antiaromatic Compounds and Antiaromaticity
  • The Pi Molecular Orbitals of Benzene
  • The Pi Molecular Orbitals of Cyclobutadiene
  • Frost Circles
  • Aromaticity Practice Quizzes

19 Reactions of Aromatic Molecules

  • Electrophilic Aromatic Substitution: Introduction
  • Activating and Deactivating Groups In Electrophilic Aromatic Substitution
  • Electrophilic Aromatic Substitution - The Mechanism
  • Ortho-, Para- and Meta- Directors in Electrophilic Aromatic Substitution
  • Understanding Ortho, Para, and Meta Directors
  • Why are halogens ortho- para- directors?
  • Disubstituted Benzenes: The Strongest Electron-Donor "Wins"
  • Electrophilic Aromatic Substitutions (1) - Halogenation of Benzene
  • Electrophilic Aromatic Substitutions (2) - Nitration and Sulfonation
  • EAS Reactions (3) - Friedel-Crafts Acylation and Friedel-Crafts Alkylation
  • Intramolecular Friedel-Crafts Reactions
  • Nucleophilic Aromatic Substitution (NAS)
  • Nucleophilic Aromatic Substitution (2) - The Benzyne Mechanism
  • Reactions on the "Benzylic" Carbon: Bromination And Oxidation
  • The Wolff-Kishner, Clemmensen, And Other Carbonyl Reductions
  • More Reactions on the Aromatic Sidechain: Reduction of Nitro Groups and the Baeyer Villiger
  • Aromatic Synthesis (1) - "Order Of Operations"
  • Synthesis of Benzene Derivatives (2) - Polarity Reversal
  • Aromatic Synthesis (3) - Sulfonyl Blocking Groups
  • Birch Reduction
  • Synthesis (7): Reaction Map of Benzene and Related Aromatic Compounds
  • Aromatic Reactions and Synthesis Practice
  • Electrophilic Aromatic Substitution Practice Problems

20 Aldehydes and Ketones

  • What's The Alpha Carbon In Carbonyl Compounds?
  • Nucleophilic Addition To Carbonyls
  • Aldehydes and Ketones: 14 Reactions With The Same Mechanism
  • Sodium Borohydride (NaBH4) Reduction of Aldehydes and Ketones
  • Grignard Reagents For Addition To Aldehydes and Ketones
  • Wittig Reaction
  • Hydrates, Hemiacetals, and Acetals
  • Imines - Properties, Formation, Reactions, and Mechanisms
  • All About Enamines
  • Breaking Down Carbonyl Reaction Mechanisms: Reactions of Anionic Nucleophiles (Part 2)
  • Aldehydes Ketones Reaction Practice

21 Carboxylic Acid Derivatives

  • Nucleophilic Acyl Substitution (With Negatively Charged Nucleophiles)
  • Addition-Elimination Mechanisms With Neutral Nucleophiles (Including Acid Catalysis)
  • Basic Hydrolysis of Esters - Saponification
  • Transesterification
  • Proton Transfer
  • Fischer Esterification - Carboxylic Acid to Ester Under Acidic Conditions
  • Lithium Aluminum Hydride (LiAlH4) For Reduction of Carboxylic Acid Derivatives
  • LiAlH[Ot-Bu]3 For The Reduction of Acid Halides To Aldehydes
  • Di-isobutyl Aluminum Hydride (DIBAL) For The Partial Reduction of Esters and Nitriles
  • Amide Hydrolysis
  • Thionyl Chloride (SOCl2)
  • Diazomethane (CH2N2)
  • Carbonyl Chemistry: Learn Six Mechanisms For the Price Of One
  • Making Music With Mechanisms (PADPED)
  • Carboxylic Acid Derivatives Practice Questions

22 Enols and Enolates

  • Keto-Enol Tautomerism
  • Enolates - Formation, Stability, and Simple Reactions
  • Kinetic Versus Thermodynamic Enolates
  • Aldol Addition and Condensation Reactions
  • Reactions of Enols - Acid-Catalyzed Aldol, Halogenation, and Mannich Reactions
  • Claisen Condensation and Dieckmann Condensation
  • Decarboxylation
  • The Malonic Ester and Acetoacetic Ester Synthesis
  • The Michael Addition Reaction and Conjugate Addition
  • The Robinson Annulation
  • Haloform Reaction
  • The Hell–Volhard–Zelinsky Reaction
  • Enols and Enolates Practice Quizzes
  • The Amide Functional Group: Properties, Synthesis, and Nomenclature
  • Basicity of Amines And pKaH
  • 5 Key Basicity Trends of Amines
  • The Mesomeric Effect And Aromatic Amines
  • Nucleophilicity of Amines
  • Alkylation of Amines (Sucks!)
  • Reductive Amination
  • The Gabriel Synthesis
  • Some Reactions of Azides
  • The Hofmann Elimination
  • The Hofmann and Curtius Rearrangements
  • The Cope Elimination
  • Protecting Groups for Amines - Carbamates
  • The Strecker Synthesis of Amino Acids
  • Introduction to Peptide Synthesis
  • Reactions of Diazonium Salts: Sandmeyer and Related Reactions
  • Amine Practice Questions

24 Carbohydrates

  • D and L Notation For Sugars
  • Pyranoses and Furanoses: Ring-Chain Tautomerism In Sugars
  • What is Mutarotation?
  • Reducing Sugars
  • The Big Damn Post Of Carbohydrate-Related Chemistry Definitions
  • The Haworth Projection
  • Converting a Fischer Projection To A Haworth (And Vice Versa)
  • Reactions of Sugars: Glycosylation and Protection
  • The Ruff Degradation and Kiliani-Fischer Synthesis
  • Isoelectric Points of Amino Acids (and How To Calculate Them)
  • Carbohydrates Practice
  • Amino Acid Quizzes

25 Fun and Miscellaneous

  • A Gallery of Some Interesting Molecules From Nature
  • Screw Organic Chemistry, I'm Just Going To Write About Cats
  • On Cats, Part 1: Conformations and Configurations
  • On Cats, Part 2: Cat Line Diagrams
  • On Cats, Part 4: Enantiocats
  • On Cats, Part 6: Stereocenters
  • Organic Chemistry Is Shit
  • The Organic Chemistry Behind "The Pill"
  • Maybe they should call them, "Formal Wins" ?
  • Why Do Organic Chemists Use Kilocalories?
  • The Principle of Least Effort
  • Organic Chemistry GIFS - Resonance Forms
  • Reproducibility In Organic Chemistry
  • What Holds The Nucleus Together?
  • How Reactions Are Like Music
  • Organic Chemistry and the New MCAT

26 Organic Chemistry Tips and Tricks

  • Common Mistakes: Formal Charges Can Mislead
  • Partial Charges Give Clues About Electron Flow
  • Draw The Ugly Version First
  • Organic Chemistry Study Tips: Learn the Trends
  • The 8 Types of Arrows In Organic Chemistry, Explained
  • Top 10 Skills To Master Before An Organic Chemistry 2 Final
  • Common Mistakes with Carbonyls: Carboxylic Acids... Are Acids!
  • Planning Organic Synthesis With "Reaction Maps"
  • Alkene Addition Pattern #1: The "Carbocation Pathway"
  • Alkene Addition Pattern #2: The "Three-Membered Ring" Pathway
  • Alkene Addition Pattern #3: The "Concerted" Pathway
  • Number Your Carbons!
  • The 4 Major Classes of Reactions in Org 1
  • How (and why) electrons flow
  • Grossman's Rule
  • Three Exam Tips
  • A 3-Step Method For Thinking Through Synthesis Problems
  • Putting It Together
  • Putting Diels-Alder Products in Perspective
  • The Ups and Downs of Cyclohexanes
  • The Most Annoying Exceptions in Org 1 (Part 1)
  • The Most Annoying Exceptions in Org 1 (Part 2)
  • The Marriage May Be Bad, But the Divorce Still Costs Money
  • 9 Nomenclature Conventions To Know
  • Nucleophile attacks Electrophile

27 Case Studies of Successful O-Chem Students

  • Success Stories: How Corina Got The The "Hard" Professor - And Got An A+ Anyway
  • How Helena Aced Organic Chemistry
  • From a "Drop" To B+ in Org 2 – How A Hard Working Student Turned It Around
  • How Serge Aced Organic Chemistry
  • Success Stories: How Zach Aced Organic Chemistry 1
  • Success Stories: How Kari Went From C– to B+
  • How Esther Bounced Back From a "C" To Get A's In Organic Chemistry 1 And 2
  • How Tyrell Got The Highest Grade In Her Organic Chemistry Course
  • This Is Why Students Use Flashcards
  • Success Stories: How Stu Aced Organic Chemistry
  • How John Pulled Up His Organic Chemistry Exam Grades
  • Success Stories: How Nathan Aced Organic Chemistry (Without It Taking Over His Life)
  • How Chris Aced Org 1 and Org 2
  • Interview: How Jay Got an A+ In Organic Chemistry
  • How to Do Well in Organic Chemistry: One Student's Advice
  • "America's Top TA" Shares His Secrets For Teaching O-Chem
  • "Organic Chemistry Is Like..." - A Few Metaphors
  • How To Do Well In Organic Chemistry: Advice From A Tutor
  • Guest post: "I went from being afraid of tests to actually looking forward to them".

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Case Studies Of Successful Students

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From The Blog

Reaction maps now available.

Reaction Maps Now Available

350 Examples of Classic Org 1/Org 2 Reactions From “Organic Syntheses”

350 Examples of Classic Org 1/Org 2 Reactions From “Organic Syntheses”

Organic Chemistry GIFS – Resonance Forms

Organic Chemistry GIFS – Resonance Forms

James Ashenhurst

Founder, master organic chemistry.

After doing a Ph. D. in organic synthesis at McGill and a postdoc at MIT, I applied for faculty positions at universities during the Great Recession. It didn’t work out. But having seen first-hand how many people struggled with the subject (including myself when I took it as an undergraduate) I thought there was a need for an online organic chemistry resource that had all the rigor of a traditional textbook, but was more approachable and accessible.

Drawing on the experience of thousands of hours spent tutoring students 1-on-1, as well as dozens of case studies, Master Organic Chemistry aims to fill in some of the conceptual gaps that aren’t traditionally covered by textbooks, and provide a friendly, logical and thorough pathway for learning introductory organic chemistry.

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Chemistry Steps

Chemistry Steps

Organic Chemistry

Doing practice problems is the only way to master organic chemistry! At Chemistry Steps, you can find all the topics of Organic 1 and 2 and their associated   practice problems . There are more than 1000 practice questions and you can find them after each article listed below.

Here are some examples from the topics shown below. 

Note : These are sample practice problems for the new users. Please go to the topics and where you can practice problems after the articles or in a separate post. 

Registered members can access all the quizzes and their solutions too.

Organic Chemistry 1 Practice Problems

Structure and bonding practice problems.

Convert the following condensed structures into  Bond-line structures :

a) CH 3 CONHCH 2 OCH 3

b) O(CH 2 ) 3 CHCH 3

c) CH 3 CHCHN(CH 3 )CH 2 CH 3

d) (CH 3 ) 3 CCH 2 CH 2 COOCH 2 CH 3

e) CH 3 CH 2 CCCH 2 CO(CH 2 ) 2 N(CH 3 ) 2

f) CH 3 CH 2 C(CH 3 )CHCH(CH 2 ) 4

g) (CH 3 ) 2 CCHCH 2 OCH(CH 3 )CH 2 CN

h) CH 3 CH 2 CHClCHBrCH 2 CONHCH(CH 3 ) 2

i) (CH 3 ) 2 CHCCCH 2 OCH(CH 2 Br)CH 2 CH 3

j) CH 3 NHCHCCH 3 CHClCON(C 2 H 5 ) 2

Answers and Solutiuons

Molecular Representations

Practice Problems

Identify the delocalized  lone pairs of electrons  for each of the following compounds and draw at least one  resonance structure  using the delocalized lone pairs.

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Answers and Solutions

Acids and Bases Practice Problems

organic chemistry homework

Alkanes and Cycloalkanes Practice Problems

Draw both chair conformation (ring-flip) and use the table to calculate the relative energy cost associated with each group in the axial position to determine the more stable chair conformation of each of the following compounds:

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Stereochemistry Practice Problems

Determine if each of the following alkenes has an  E  or  Z   configuration:

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Determine the relationship in each of the following pairs. Do the drawings represent  constitutional isomers  or stereoisomers, or are they just different ways of drawing the same compound? If they are stereoisomers, are they  enantiomers  or diastereomers? Explain your answer by converting the drawings into the same representation, i.e. if you are comparing a  Newman projection  to a  Fischer projection , you need to convert both into either a Newman or Fischer projection. Assign all the  absolute configurations as  R  or  S  if you hesitate.

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Identify all the chiral centers in each molecule and determine the absolute configuration as  R  or  S :

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Nucleophilic Substitution and Elimination Reactions

Predict the mechanism as SN1, SN2, E1 or E2 and draw the major organic product formed in each reaction. Consider any regioselectivity and stereoselectivity where applicable:

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Reactions of Alkenes Practice Problems

Identify the reagents for each of the following addition reaction to an alkene:

organic chemistry homework

Predict the product(s) that are formed after each step for reactions  A-G . In each case, consider formation of any chiral center(s) and draw all expected stereoisomers.

This is a comprehensive problem that covers the following topics and will serve as a review of all of them:

Substitution and elimination reactions.  Particularly,  substitution and elimination reactions of alcohols , the  regio – and stereochemistry of E2 reactions and E2  reaction of cyclohexanes .

Mesylation and tosylation in Substitution and elimination reactions. 

Hydrohalogenation of alkenes according to the Markovnikov’s rule .

Radical hydrohalogenation of alkenes .

Hydroboration-Oxidation of Alkenes .

Halogenation of alkenes through halohydrin formation .

Syn and anti dihydroxilation of alkenes.

Elimination reactions: Zaitsev and Hoffman products .

Ozonoloysis of Alkenes.

organic chemistry homework

Attempt solving the entire problem before accessing the answers!

The  answers  will give you the structure of the  final product(s) only . Use this as a hint to determine the compounds formed after the first and second reactions.

Reactions of Alkynes Practice Problems

Identify the reagents for each of the following reactions of internal and terminal alkynes:

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On the following synthetic scheme, identify the reagents, in the correct order, that you would use to achieve the following synthetic transformations. Determine the structure of compounds A and B and the major organic products resulting from the alkyne.

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Organic Chemistry 2 Practice Problems

Nmr spectroscopy practice problems.

The  1 H NMR spectrum of compound X ( C 4 H 8 O 2 ) is shown below. It also shows a strong IR absorption band near 1730 cm −1 . Propose a structure for  X .

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IR Spectroscopy

Label the functional groups and identify the correct compound based on the IR spectrum.

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Radicals Practice Problems

Predict the products when each of the following compounds is treated with NBS under UV light:

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Alcohols Practice Problems

Predict the major organic product(s) for the following Grignard reactions of a ketone, aldehyde, ester, carbon dioxide and an epoxide:

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Predict the major organic product when the following alcohol is treated with each oxidizing agent:

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The Diels-Alder Reaction Practice Problems

For each Diels–Alder reaction, predict the major product(s) with correct stereochemistry when each cyclic  diene is reacted with a dienophile:

organic chemistry homework

Aromatic Substitution Practice Problems

Show how each compound can be synthesized from benzene and any other organic or inorganic reagents.

The order of reactions is very important!  So, before every step,  consider the ortho – ,  para – ,  or meta directing effect  of the current group on the aromatic ring.

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Devise a synthesis of each of the following compounds using an arene diazonium salt. They all require more than one step and you may select the desired regioisomer (for example the para product from an ortho, para mixture) when needed.

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Aldehydes and Ketones Practice Problems

Predict the major product(s) obtained when each of the following compounds undergoes hydrolysis in the presence of an acid:

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 Carboxylic Acids and Their Derivatives Practice Problems

Predict the  major organic product(s)  for each of the following reactions. They  all involve carboxylic acid derivatives  such as  esters, acid chlorides, nitriles, anhydrides, and amides . You may also need to go over the reactions covered in earlier chapters, particularly, the  Grignard  and  Gilman  reagents,  oxidizing  and  reducing   agents  and  electrophilic aromatic substitutions .

A link to each topic encountered in a given problem will be provided in the answer tab.

organic chemistry homework

Alpha Carbon Chemistry – Enols and Enolates Practice Problems

his is a  comprehensive practice problem  on the alpha carbon chemistry. The topics covered range from the simple halogenation reactions of enols to  multistep synthetic transformation .

To correctly answer these questions, you need to review the main principles of enolate chemistry – direct enolate alkylation, aldol condensation, crossed aldol condensation, alkylation using acetoacetic ester synthesis, malonic ester synthesis, the Stork enamine synthesis, Claisen condensation, Michael addition, and Robinson annulation.

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Check out our new synthesis puzzles!

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CS Prime membership will also grant you access to multiple-choice quizzes!

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General Chemistry Overview Quiz

Molecular representations quiz, organic acids and bases quiz, alkanes and cycloalkanes practice quiz, stereochemistry practice problems quiz, nucleophilic substitution and elimination practice quiz, alkene addition reactions practice quiz, alkyne naming and reactions practice quiz, organic chemistry final practice quiz.

Aromatic Compounds

Alcohols Quiz – Naming, Preparation, and Reactions

Aldehydes and ketones reactions practice quiz, carboxylic acids and their derivatives quiz, carbohydrates practice problem quiz, iupac nomenclature summary quiz.

Table of Content

Structure and Bonding

  • Lewis Structures in Organic Chemistry
  • Valency and Formal Charges in Organic Chemistry
  • sp3, sp2, and sp Hybridization in Organic Chemistry with Practice Problems
  • How to Quickly Determine The sp3, sp2 and sp Hybridization
  • Molecular and Electron Geometry of Organic Molecules with Practice Problems
  • Bond-Line or Skeletal Structures
  • Functional Groups in Organic Chemistry
  • Converting between Bond-line, Lewis and Condensed Structures with Practice Problems
  • Curved Arrows with Practice Problems
  • Resonance Structures in Organic Chemistry
  • How to Choose the More Stable Resonance Structure
  • Drawing Complex Patterns in Resonance Structures
  • Localized and Delocalized Lone Pairs with Practice Problems

Acids and Bases

Organic Acids and Bases

  • Organic acid-base mechanisms
  • Acid Strength and pKa
  • How to Determine the Position of Equilibrium for an Acid–Base Reaction
  • Factors That Determine the pKa and Acid Strength
  • How to Choose an Acid or a Base to Protonate or Deprotonate a Given Compound
  • Lewis Acids and Bases

Alkanes and Cycloalkanes

  • Naming Alkanes by IUPAC nomenclature Rules Practice Problems
  • How to Name a Compound with Multiple Functional Groups
  • Primary Secondary and Tertiary Carbon Atoms in Organic Chemistry
  • Constitutional or Structural Isomers with Practice Problems
  • Degrees of Unsaturation or Index of Hydrogen Deficiency
  • Newman Projections with Practice Problems
  • Gauche Conformation, Steric, Torsional Strain Energy Practice Problems
  • Drawing the Chair Conformation of Cyclohexane
  • Ring Flip: Drawing Both Chair Conformations with Practice Problems
  • 1,3-Diaxial Interactions and A value for Cyclohexanes
  • Ring-Flip: Comparing the Stability of Chair Conformations with Practice Problems
  • Cis and Trans Decalin

Stereochemistry

  • Enantiomers Diastereomers the Same or Constitutional Isomers with Practice Problems
  • Chirality and Enantiomers: Determine if Enantiomers or Identical based on R and S Configuration
  • Cis and Trans Stereoisomerism in Alkenes
  • E and Z Alkene Configuration with Practice Problems
  • How to Determine the R and S configuration
  • The R and S Configuration Practice Problems
  • Determine the Relationship – Enantiomers Diastereomers or Constitutional Isomers
  • Optical Activity
  • Enantiomeric Excess (ee): Percentage of Enantiomers from Specific Rotation with Practice Problems
  • Calculating Enantiomeric Excess from Optical Activity
  • Symmetry and Chirality. Meso Compounds
  • Fischer Projections with Practice Problems
  • Resolution of Enantiomers: Separate Enantiomers by Converting to Diastereomers

Nucleophilic Substitution Reactions

  • SN1 SN2 E1 E2 – How to Choose the Mechanism
  • Is it SN1 SN2 E1 or E2 Mechanism With the Largest Collection of Practice Problems
  • Introduction to Alkyl Halides
  • Nomenclature of Alkyl Halides
  • Introduction to Substitution Reactions
  • All You Need to Know About the S N 2 Reaction Mechanism
  • The SN2 Mechanism: Kinetcis, Thermodynamics, Curved Arrows and Stereochemistry with Practice Problems
  • Mechanism and Stereochemistry of SN2 Reactions with Practice Problems
  • Mesylates and Tosylates as Good Leaving Groups
  • SOCl 2 and PBr 3 for Conversion of Alcohols to Alkyl Halides
  • The SN1 Nucleophilic Substitution Reaction
  • The SN1 Mechanism: Kinetcis, Thermodynamics, Curved Arrows and Stereochemistry with Practice Problems
  • The Substrate and Nucleophile in SN2 and SN1 Reactions
  • The Role of the Solvent in SN1, SN2, E1 and E2 Reactions
  • Carbocation Rearrangements in SN1 Reactions with Practice Problems
  • When Is the Mechanism SN1 or SN2?
  • How to Choose Molecules for Doing SN2 and SN1 Synthesis-Practice Problems
  • Alcohols in Substitution Reactions with Tons of Practice Problems

Alkenes: Structure, Stability and Nomenclature

  • Naming Alkenes by IUPAC Nomenclature Rules

Elimination Reactions

  • General Features of Elimination
  • The E2 Mechanism
  • Zaitsev’s Rule – Regioselectivity of E2 Elimination Reactions
  • The Hofmann Elimination of Amines and Alkyl Fluorides
  • Stereoselectivity of E2 Elimination Reactions
  • Stereospecificity of E2 Elimination Reactions
  • Elimination Reactions of Cyclohexanes with Practice Problems
  • POCl 3 for Dehydration of Alcohols
  • The E1 Mechanism: Kinetcis, Thermodynamics, Curved Arrows and Stereochemistry with Practice Problems
  • Dehydration of Alcohols by E1 and E2 Elimination
  • Stereoselectivity of E1 Reactions
  • Nucleophilic Substitution vs Elimination Reactions
  • Regioselectivity of E1 Reactions
  • E2 vs. E1 Elimination Mechanism with Practice Problems

Addition Reactions of Alkenes

  • Markovnikov’s Rule with Practice Problems
  • The Stereochemistry of Alkene Addition Reactions
  • Free-Radical Addition of HBr: Anti-Markovnikov Addition
  • Acid-Catalyzed Hydration of Alkenes with Practice Problems
  • Oxymercuration-Demercuration
  • Hydroboration-Oxidation: The Mechanism
  • Hydroboration-Oxidation of Alkenes: Regiochemistry and Stereochemistry with Practice Problems
  • Halogenation of Alkenes and Halohydrin Formation
  • Ozonolysis of Alkenes with Practice Problems
  • Syn Dihydroxylation of Alkenes with KMnO4 and OsO4
  • Anti Dihydroxylation of Alkenes with MCPBA and Other Peroxides with Practice Problems
  • Oxidative Cleavage of Alkenes with KMno4 and O3
  • Cis product in an anti Addition Reaction of Alkenes
  • Alkene Reactions Practice Problems
  • Changing the Position of a Double Bond
  • Changing the Position of a Leaving Group
  • Alkenes Multi-Step Synthesis Practice Problems
  • Addition of Alcohols to Alkenes
  • Introduction to Alkynes
  • Naming Alkynes by IUPAC Nomenclature Rules – Practice Problems
  • Preparation of Alkynes by Elimination Reactions
  • Hydrohalogenation of Alkynes
  • Acid Catalyzed Hydration of Alkynes with Practice Problems
  • Reduction of Alkynes
  • Halogenation of Alkynes
  • Hydroboration-Oxidation of Alkynes with Practice Problems
  • Ozonolysis of Alkynes with Practice Problems
  • Alkylation of Terminal Alkynes in Organic Synthesis with Practice Problems
  • Alkyne reactions summary practice problems
  • Alkyne Synthesis Reactions Practice Problems

Nuclear Magnetic Resonance (NMR) Spectroscopy

  • NMR spectroscopy – An Easy Introduction
  • NMR Chemical Shift
  • NMR Chemical Shift Range and Value Table
  • NMR Number of Signals and Equivalent Protons
  • Homotopic Enantiotopic Diastereotopic and Heterotopic
  • Homotopic Enantiotopic Diastereotopic Practice Problems
  • Integration in NMR Spectroscopy
  • Splitting and Multiplicity (N+1 rule) in NMR Spectroscopy
  • NMR Signal Splitting N+1 Rule Multiplicity Practice Problems
  • 13 C Carbon NMR
  • DEPT NMR: Signals and Problem Solving
  • NMR Spectroscopy-Carbon-Dept-IR Practice Problems

Organic Structure Determination

  • Infrared (IR) Spectroscopy with Lots of Real Spectrum Practice Problems

Radical Reactions

  • Initiation Propagation Termination in Radical Reactions
  • Selectivity in Radical Halogenation
  • Stability of Radicals
  • Resonance Structures of Radicals
  • Stereochemistry of Radical Halogenation with Practice Problems
  • Allylic Bromination by NBS with Practice Problems
  • Radical Halogenation in Organic Synthesis

Reactions of Alcohols

  • Nomenclature of Alcohols: Naming Alcohols based on IUPAC Rules with Practice Problems
  • Preparation of Alcohols via Substitution or Addition Reactions
  • Reaction of Alcohols with HCl, HBr and HI Acids
  • The Williamson Ether Synthesis
  • POCl 3 for Dehydration of Alcohols Alcohols in Substitution Reactions with Tons of Practice Problems
  • LiAlH4 and NaBH4 Carbonyl Reduction Mechanism
  • Alcohols from Carbonyl Reductions – Practice Problems
  • Grignard Reaction in Preparing Alcohols with Practice Problems
  • Grignard Reaction in Organic Synthesis with Practice Problems
  • Protecting Groups For Alcohols and Their Use in Organic Synthesis
  • Oxidation of Alcohols: PCC, PDC, CrO3, DMP, Swern and All of That
  • NaIO4 Oxidative Cleavage of Diols
  • Preparation of Epoxides
  • Reactions of Epoxides Practice Problems

Conjugated Systems

  • Resonance and Conjugated Dienes
  • Allylic Carbocations
  • 1,2 and 1,4 Electrophilic Addition to Dienes
  • Kinetic vs Thermodynamic Control of Electrophilic Addition to Dienes

The Diels-Alder Reaction

  • Diels Alder Reaction: Dienes and Dienophiles
  • Predict the Products of the Diels-Alder Reaction with Practice Problems
  • Endo and Exo products of Diels-Alder Reaction with Practice Problems
  • Regioselectivity of the Diels–Alder Reaction with Practice Problems
  • Identify the Diene and Dienophile of the Diels–Alder Reaction with Practice Problems
  • Diels Alder Reaction in Organic Synthesis Practice Problems
  • Naming Aromatic Compounds
  • Introduction to Aromatic Compounds
  • Benzene – Aromatic Structure and Stability
  • Aromaticity and Huckel’s Rule
  • Identify Aromatic, Antiaromatic, or Nonaromatic Compounds

Electrophilic Aromatic Substitution

  • Electrophilic Aromatic Substitution – The Mechanism
  • Friedel-Crafts Alkylation with Practice Problems
  • Friedel-Crafts Acylation with Practice Problems
  • The Alkylation of Benzene by Acylation-Reduction
  • Ortho Para Meta Directors in Electrophilic Aromatic Substitution with Practice Problems
  • Ortho Para and Meta in Disubstituted Benzenes
  • Why Are Halogens Ortho-, Para- Directors yet Deactivators ?
  • Limitations on Electrophilic Aromatic Substitution Reactions
  • Orientation in Benzene Rings With More Than One Substituent
  • Synthesis of Aromatic Compounds From Benzene
  • Electrophilic Aromatic Substitution with Arenediazonium Salts
  • Reactions at the Benzylic Position

Nucleophilic Aromatic Substitution

Aldehydes and Ketones

  • Nomenclature of Aldehydes and Ketones
  • Preparation of Aldehydes and Ketones
  • Nucleophilic Addition to Carbonyl Groups
  • The Addition-Elimination Mechanism
  • Reduction of Carbonyl Compounds by Hydride Ion
  • Reactions of Aldehydes and Ketones with Water
  • Reactions of Aldehydes and Ketones with Alcohols: Acetals and Hemiacetals
  • Acetals as Protecting Groups for Aldehydes and Ketones
  • Imines from Aldehydes and Ketones with Primary Amines
  • Enamines from Aldehydes and Ketones with Secondary Amines
  • Reactions of Aldehydes and Ketones with Amines-Practice Problems
  • Acetal Hydrolysis Mechanism
  • Imine and Enamine Hydrolysis Mechanism
  • The reaction  of Aldehydes and Ketones with CN Cyanohydrin Formation
  • Hydrolysis of Acetals, Imines and Enamines-Practice Problems
  • The Wittig Reaction: Examples and Mechanism
  • The Wittig Reaction-Practice Problems

Carboxylic Acids and Their Derivatives-Nucleophilic Acyl Substitution

  • Preparation of Carboxylic Acids
  • Fischer Esterification
  • Ester Hydrolysis by Acid and Base-Catalyzed Hydrolysis
  • What is Transesterification?
  • Esters Reaction with Amines – The Aminolysis Mechanism
  • Ester Reactions Summary and Practice Problems
  • Preparation of Acyl (Acid) Chlorides (ROCl)
  • Reactions of Acid Chlorides (ROCl) with Nucleophiles
  • Reaction of Acyl Chlorides with Grignard and Gilman (Organocuprate) Reagents
  • Reduction of Acyl Chlorides by LiAlH4, NaBH4, and LiAl(OtBu)3H
  • Preparation and Reaction Mechanism of Carboxylic Anhydrides
  • Amides – Structure and Reactivity
  • Amides Hydrolysis: Acid and Base-Catalyzed Mechanism
  • Amide Dehydration Mechanism by SOCl2, POCl3, and P2O5
  • Amide Reduction Mechanism by LiAlH4
  • Amides Preparation and Reactions Summary
  • Amides from Carboxylic Acids-DCC and EDC Coupling
  • The Mechanism of Nitrile Hydrolysis To Carboxylic Acid
  • Nitrile Reduction Mechanism with LiAlH4 and DIBAL to Amine or Aldehyde
  • The Mechanism of Grignard and Organolithium Reactions with Nitriles
  • Carboxylic Acids and Their Derivatives Practice Problems

Alpha Carbon Chemistry: Enols and Enolates

  • Alpha Halogenation of Enols and Enolates
  • The Haloform and Iodoform Reactions
  • Alpha Halogenation of Carboxylic Acids
  • Alpha Halogenation of Enols and Enolates Practice Problems
  • Aldol Reaction – Principles and Mechanism
  • Aldol Condensation – Dehydration of Aldol Addition Product
  • Intramolecular Aldol Reactions
  • Aldol Addition and Condensation Reactions – Practice Problems
  • Crossed Aldol And Directed Aldol Reactions
  • Crossed Aldol Condensation Practice Problems
  • Alkylation of Enolates Alpha Position
  • Enolate Alkylation Practice Problems
  • Acetoacetic Ester Synthesis
  • Acetoacetic Ester Enolates Practice Problems
  • Malonic Ester Synthesis
  • Michael Reaction: The Conjugate Addition of Enolates
  • Robinson Annulation, Shortcut, and Retrosynthesis
  • Claisen Condensation
  • Dieckmann condensation – An Intramolecular Claisen Reaction
  • Crossed Claisen and Claisen Variation Reactions
  • Claisen Condensation Practice Problems
  • Stork Enamine Synthesis
  • Enolates in Organic Synthesis – a Comprehensive Practice Problem
  • Preparation of Amines
  • The Gabriel Synthesis of Primary Amines
  • The Reaction of Amines with Nitrous Acid
  • Reactions of Amines Practice Problems

Organic Synthesis Problems

  • Organic Chemistry Multistep Synthesis Practice Problems

All the practice problems are  open to everyone for free!  I have seen and prepared hundreds of exams for organic chemistry and these practice problems are the types that  you will find in your exams . Their difficulty varies from one-step to more advanced ones including step organic synthesis problems.

After working on each question, you have the possibility to first check your  answer   and then refer to the  step-by-step  solution .

organic chemistry homework

The practice problems are the only ones you get to do.

Multiple choice quizzes might be the “easy” way of glancing through the key concepts and getting feedback on what you need to work more.

These are also included in your Chemistry Steps membership.

Energy Changes In Organic Chemistry

NMR Spectroscopy

Infrared (IR) Spectroscopy

Ethers and Epoxides

Carboxylic Acids and Their Derivatives

Enolates in Organic Synthesis

Reactions of Amines

Synthesis Maps

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The blog posts you find here combine clear written explanations and diagrams with key concept videos, plus interactive quizzes to help you assess how you’re going and cutting-edge, interactive 3D models of key molecules.

Here you’ll find clear, easy-to-follow explanations of the Organic Chemistry concepts your Professor wants you to know, and exam-style practice questions, worked answers and in-depth videos explaining how to tackle even the most challenging or Organic Chemistry exam questions. When you get to the exam, you’ll feel like you’ve seen it all before!

The following problems are meant to be useful study tools for students involved in most undergraduate organic chemistry courses.  The problems have been color-coded to indicate whether they are:

1.   Generally useful , 2.   Most likely to be useful to students in year long, rather than survey courses , 3.   Most likely to be useful only to students in courses for chemistry majors and/or honors students .

Some of these problems make use of a Molecular Editor drawing application.  To practice using this editor Click Here .

Most of these Interactive Organic Chemistry Practice Problems have been developed by Professor William Reusch. �1999 William Reusch, All rights reserved. Comments, questions and errors should be sent to [email protected] . The Virtual Text and some of the problems make use of either the CHIME plugin , or Jmol . Click on the name for information and a free copy. If possible, monitor resolutions of 1024 x 768 or 1152 x 870 should be used.

Department of Chemistry Michigan State University East Lansing, MI  48824

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  • General Chemistry Review (Select Topics)
  • Representing Organic Molecules (Structure and Bonding)
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  • Alkanes and Cycloalkanes
  • Chirality and Isomerism
  • Haloalkanes (Alkyl Halides)
  • Nucleophilic Substitutions and Elimination Reactions
  • Alkenes: Structure and Properties
  • Reactions of Alkenes
  • Alkynes: Structure, Properties, and Synthesis
  • Conjugated Pi Systems, Dienes, and Resonance
  • Aromaticity and Benzene
  • Reactions of Benzene and its Derivatives
  • Pericyclic Reactions and Orbital Interactions
  • Alcohols and Phenols
  • Ethers, Epoxides, Thiols, and Sulfides
  • Aldehydes and Ketones
  • Enols, Enolates, Enamines: Alpha-Carbon Chemistry
  • Introduction to Organometallic Chemistry
  • Carboxylic Acids
  • Carboxylic Acid Derivatives and Nitriles
  • Amines and Heterocycles
  • Synthetic Polymers (Organic Polymers)
  • Structure Determination: UV-Vis Spectroscopy
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  • Nuclear Magnetic Resonance (NMR) Spectroscopy
  • Combined Spectroscopy Problems
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  • Biomolecules: Amino Acids, Peptides, and Proteins
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You have incorrectly assigned the configuration. Evaluate the 4 atoms directly attached to the stereocenter using the Cahn-Ingold-Prelog (CIP) rules to determine the configuration of the stereocenter and try again.

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The total number of carbons in the parent chain of your product is incorrect. Consider how the the presence of the nitrile group in reaction step 1 modifies to the original parent carbon chain.

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  • Chirality and Isomerism
  • Haloalkanes (Alkyl Halides)
  • Nucleophilic Substitutions and Elimination Reactions
  • Alkenes: Structure and Properties
  • Reactions of Alkenes
  • Alkynes: Structure, Properties, and Synthesis
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  • Introduction to Organometallic Chemistry
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  • Synthetic Polymers (Organic Polymers)
  • Structure Determination: UV-Vis Spectroscopy
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  • Biomolecules: Enzymes
  • Biomolecules: Nucleic Acids and Protein Synthesis

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Help students master both IUPAC and common naming of every functional group in Organic Chemistry.

Assign nomenclature problems outside of class to save more class time for higher order topics like synthesis and mechanisms.

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