Organic Structures

Nomenclature

Introduction/Overview/Beginner

An Introduction to Basic Organic Nomenclature (Dave Woodcock, Okanagan University College): This is a overview of naming organic compounds using the IUPAC Systematic Approach to Nomenclature.

Wikipedia page on IUPAC nomenclature

Master Organic Chemistry Nomenclature

Nomenclature101 (University of Ottawa): Tools to identify functional groups and draw molecules; design your own quizzes from their question pool.

Application/Intermediate/Applied

Extra Nomenclature Exercises:

Organic Chemistry Problems (Michigan State University): This website has 21 nomenclature questions. Some the questions are multiple choice, but most require the student to draw a named molecule.

Basic Organic Nomenclature (McGraw-Hill): Website with 15 quizzes that cover different functional groups.

More Quizzes (University of Guelph): One multiple-choice quiz and two free answer quizzes.

Naming Alkanes: This website generates random alkanes and when prompted provides hints and the name.

Oxidation-Reduction Equations

Introduction/Overview/Beginner

Redox This website contains power point slides explaining how to balance redox equations using half-reactions.

Mr.Kent This video shows how to balance redox equations using half-reactions. (Video)

Determining Organic Structures

Mass Spectrometry

Introduction/Overview/Beginner

Cal State Chemistry Tutorials This website contains basic information regarding mass spectrometry.

An Introduction to Mass Spectrometry(Dr.Alison E. Ashcroft) This website contains basic information regarding mass spectrometry.

Intermediate/More Detail

Scripps Center This is the website for Scripps Center for Metabolomics and Mass Spectrometry, it contains a more detailed or advanced description of mass spectrometry.

Extra Information

Mass Spectrometry As short YouTube video demonstrating a application of mass spectroscopy.

Electron Impact (University of Birmingham) This website provides information on Electron Impact, a way of producing ions used in mass spectrometry.

NIST This database allows you to search for a mass spectrum using the molecular formula.

SDBS This database allows you to search for a mass spectrum using the molecular formula.

 

13C NMR

Introduction/Overview/Beginner

13C-NMR Intro (Dr. S. Bruce King, Dr. Yue-Ling Wong, Wake Forest University) This website gives a basic introduction to 13C-NMR. It also includes a few practice problems. (REQUIRES SHOCKWAVE)

Nuclear Magnetic Resonance Spectroscopy (Michigan State University) This website provides a thorough overview of 13C NMR spectroscopy including how to read 13C NMR spectroscopy. (Practice Problems at the bottom of webpage)

Intermediate/More Detail

Minnesota NMR Center (University of Michigan) This website has several links that provide a more detailed background about NMR spectroscopy and its applications.

Extra Information

SDBS This database allows you to search for NMR spectra using the molecular formula.

Table of Solvent Signals (University of California Los Angeles) This website host a table that list the chemical shifts of common solvents.

 

Infrared Spectra

Introduction/Overview/Beginner

Video Tutorial (Royal Society of Chemistry) This is a video provides a general introduction to infrared spectrometry. (VIDEO)

IR Spectroscopy Tutorial (University of Colorado Boulder) This website provides detailed information on identifying particular functional groups using infrared spectrometry.

Extra Information

SDBS This database allows you to search for an infrared spectrum using the molecular formula.

Extra Problems

Nuclear Magnetic Resonance Spectroscopy This website provides practice problems at the bottom of the page.

WebSpectra Problems in NMR and IR Spectroscopy (Professor Craig A. Merlic and Dr. Jane Strouse, University of California Los Angeles) This website contains NMR and IR spectroscopy problems. Difficulty ranges from beginner to advanced.

Delocalization and Conjugation

Introduction/Overview/Beginner

Chemistry Wiki: This page contains a brief overview of delocalized electrons. This page is better organized than the Wikipedia page on delocalization.

Wikipedia: Delocalization: This is the Wikipedia page for delocalization.

Wikipedia: Conjugation: This is the Wikipedia page for conjugation.

 

Master Organic Chemistry

Resonance

Curved Arrows

Resonance Forms

Electronegativity

Negative Charge

Positive Charge

Summary of Resonance

 

Intermediate/More Detail

Conjugated Dienes

Delocalization and π Bonds: This link goes into detail about stability, resonance, and molecular orbital theory of adjacent p orbitals.

 

 

Acidity, basicity, and pKa

Introduction/Overview/Beginner

 

Brønsted-Lowry

Brønsted Concept of Acids and Bases: The webpage defines a Brønsted-Lowry Acid and Base. It also provides links to outside websites that provide more in depth information on Brønsted acids and bases.

Brønsted Concept of Acids and Bases: This video provides a brief overview of the bronsted0lowery concept of an acid and base.

 

Lewis

Lewis Concept of Acids and Bases: The webpage defines a Brønsted-Lowry Acid and Base. It also provides links to outside websites that provide more in depth information to Lewis acids and bases

 

Both

Theories of Acids and Bases: This video gives an overview of both Brønsted- Lowry theory of acids and bases and Lewis theory of acids and bases.

 

Intermediate/More Detail

pKa Table

pKb Table

Combined pKa and pKb table

Henderson-Hasselbalch

solubility of acids; solubility of their conjugate bases

Nucleophilic substitution at the carbonyl (C=O) group

Introduction/Overview/Beginner

Wikipedia: This page provides an overview of carbonyl groups.

Wikipedia: This page provides an overview of nucleophilic substitution.

Chemistry Wikipedia: This page provides an overview of carbonyl substitution.

Intermediate

Nucleophilic Substitution: This page provides an overview of nucleoophilc substitution. It goes into detail on nucleophilic substitutions that involve Hydroxide Ions, Water, Cyanide Ions, and Ammonia.

EXTRA STUFF

Table of Carboxylic Acid Derivatives

TABLE OF REACTIVITY (public site)

Nucleophilic Acyl Substitution: This is video explanation of a general nucleophilic substitution at the carbonyl.

Fischer Esterification: This is a video explanation of an important nucleophilic substitution.

Nucleophilic substitution at C=O with loss of carbonyl oxygen

Introduction/Overview/Beginner

Formation of Acetals: This page contains examples and explanations of the formation of hemiacetals, acetals, cyclic hemiacetal, cyclic acetals, and acetals as protecting groups.

Reaction with Primary Amines to form Imines: This page contains examples and explanations of primary amines reacting to form imines. (Practice Problems)

 

http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Emphasis/Chapter_11%3A_Nucleophilic_carbonyl_addition_reactions/Section_11.6%3A_Imine_(Schiff_base)_formation

 

Wittig Reaction: This page contains the examples and an explanation of the Wittig reaction. (Practice Problems)

 

Video Resources

Stereochemistry

UCDavis ChemWIki

 

Enantiomers: This page contains an explanation of enantiomers, stereogenic nitrogen and R/S nomenclature.

Chirality: This page contains an explanation of the spatial arrangement of at

Newman Projection: This page contains an explanation of Newman projection.

Fischer Projection: This page contains an explanation of Fischer projection.

Stereocenter: This page contains an explanation of Stereogenic centers.

Master Organic Chemistry

Chiral Allenes and Chiral Axes

 

On Cats Part One: This page uses cats to teach conformations of molecules and constitutional isomers.

On Cats Part Two: This page uses cats to teach line-angle diagram and rotations.

On Cats Part Three: This page uses cats to teach Newman projection.

On Cats Part Four: This page uses cats to teach about Enantiomers.

On Cats Part Five: This page uses cats teach about enantiomers and diastereomers.

On Cats Part Six: This page uses cats to teach about stereocenters.

On Cats Part Seven: This Page uses cats to teach about the Fischer projection.

Nucleophilic substitution at saturated carbon

 

Nucleophile

The SN1 Mechanism: This page contains a detailed explanation of SN1 reactions including transition states and stereochemistry.

The SN2 Mechanism: This page contains a detailed explanation of SN2 reactions including transition states and stereochemistry.

When Is the Mechanism SN1 or SN2?: This page contains a handy guide to determining if a reactions mechanism is SN1 or SN2.

 

Master Organic Chemistry

Walkthrough of Substitution Reactions (1) – Introduction

Two Types of Substitution Reactions

The SN1 Mechanism

The SN2 Mechanism

Comparing the SN1 and SN2 Reactions

Elimination reactions

UCDavis ChemWIki

A General Overview of E1 Elimination: This page provides a general overview of the E1 Mechanism.

Elimination by the E1 Mechanism: This page provides a detailed description of the E1 mechanism, the stereochemistry that results from the E1 mechanism, and the order of reactivity of carbocations.

A General Overview of E2 Elimination: This page provides a general overview of the E2 Mechanism.

Elimination by the E2 Mechanism: This page provides a detailed description of the E2 mechanism and the stereochemistry that results from the E2 mechanism.

Elimination v. Substitution: This page provides a general methodology for determining if a halogenoalkane will under go an elimination reaction or a substitution reaction.

 

Master Organic Chemistry

Walkthrough of Elimination Reactions

Two Types of Elimination Reactions

The E1 Mechanism

The E2 Mechanism

Comparing E1 and E2 Reactions

Deciding SN1/SN2/E1/E2 (1)

Deciding SN1/SN2/E1/E2 (2)

Wrapup: The Quick N’ Dirty Guide To SN1/SN2/E1/E2