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    Organic Chemistry I – CHE 267 FALL 2018 Course Schedule

    Class Day


    Skype Assignments

    Learning Objectives

    August 27

    Introduction to course and technology

    Review General Chemistry

    (LibreText, Socrative, Skype, Collaborative Learning)

    Academic Reading Circle practice

    August 29

    Chapter 1: Structure and Bonding

    1.1 The Periodic Table

    1.2 Bonding

    1.3 Lewis Structures

    1.5 Lewis Structure Exceptions

    1.5 Resonance

    1.6 Determining Molecular Shape

    1.7 Drawing Organic Structures

    Read sections 1.1-1.7

    State number of valence electrons and bonds formed for common organic elements.

    Draw accurate Lewis structures for organic molecules (neutral and charged).

    Convert between types of structural drawings (Lewis, condensed, skeletal).

    Draw resonance forms and evaluate stability.

    August 31

    Chapter 1: Structure and Bonding

    1.8 Hybridization

    1.10 Bond Length and Bond Strength

    1.11 Electronegativity and Bond Polarity

    1.12 Polarity of Molecules

    Read sections 1.8-1.12

    Describe the hybrid orbitals used at each atom in an organic structure.

    Label the polarity of any covalent bond.

    September 3

    Labor DayNo Class

    September 5

    Chapter 2: Introduction to Organic Molecules and Functional Groups

    2.1 An Overview of Functional Groups

    2.2 Intermolecular Forces

    2.3 Physical Properties

    2.4 Application: Vitamins

    2.6 Application: The Cell Membrane

    2.7 Functional Groups and Reactivity

    2.8 Biomolecules

    Read Sections 2.1-2.8

    Identify common organic functional groups.

    Determine relative boiling points based on intermolecular forces and molecular structure.

    Determine water solubility of organic molecules based on structure.

    Explain how cell membranes use solubility to restrict molecules entering and leaving the cell.

    Identify nucleophilic and electrophilic regions of a molecule.

    September 7

    Nomenclature Read the following:

    3.3, 3.4, 3.5, 3.6, 7.2, 10.3, 11.2

    Name organic molecules using the basics of the IUPAC nomenclature system (up to 10 carbons). – including alkanes, alkenes, alkynes, alkyl halides

    Draw organic molecules given IUPAC names.

    Name simple cyclic structures.

    September 10

    Nomenclature Read the following:

    9.3, 13.3, 19.2, 21.2, 22.3, 25.3

    Name organic molecules using the basics of the IUPAC nomenclature system (up to 10 carbons). – including alcohols, ethers, ketones, aldehydes, amines, amides, esters, carboxylic acids

    Draw organic molecules given IUPAC names.

    September 12

    Chapter 3: Alkanes

    3.1 Alkanes—An Introduction

    3.2 Cycloalkanes

    3.3 An Introduction to Nomenclature

    3.4 Naming Alkanes

    3.5 Naming Cycloalkanes

    3.6 Common Names of Alkanes

    3.7 Physical Properties of Alkanes

    3.8 Conformations of Ethane

    3.9 Conformations of Butane

    Read sections 3.1-3.9

    OCA 1

    Naming alkanes and functional groups

    Assigned September 12

    Due September 19

    Reflection Due September 21

    Draw conformations of molecules in sawhorse and Newman projections.

    Determine local and global maxima and minima from Newman projections.

    September 14

    Chapter 3: Alkanes

    3.10 An Introduction to Cycloalkanes

    3.11 Cyclohexane

    3.12 Substituted Cycloalkanes

    3.13 Lipids part 1

    Read sections 3.10-3.13

    Draw chair structures of substituted cyclohexanes and ring flipped structures.

    Determine relative energies of conformational isomers of cyclohexane chair structures.

    September 17

    Exam 1 –Chapters 1-3 and Nomenclature

    September 19

    Chapter 4: Stereochemistry

    4.1 The Two Major Classes of Isomers

    4.2 Chiral and Achiral Molecules

    4.3 Stereogenic Centers

    4.4 Labeling Stereogenic Centers with R or S

    Read sections 4.1-4.4

    OCA 2

    Drawing cyclohexane structures

    Assigned September 19

    Due September 26

    Reflection Due September 28

    Define chirality, enantiomer and diastereomer.

    Identify chiral atoms in skeletal structures.

    Label stereogenic centers as R or S.

    September 21

    Chapter 4: Stereochemistry

    4.5 Diastereomers

    4.6 Meso Compounds

    4.7 R and S Assignments in Compounds with Two or More Stereogenic Centers

    4.8 Disubstituted Cycloalkanes

    4.9 Isomers—A Summary

    4.10 Physical Properties of Stereoisomers

    4.11 Chemical Properties of Enantiomers

    Read sections 4.5-4.11

    Classify pairs of compounds as enantiomer, diastereomers, meso, constitutional isomers or not isomers.

    Draw the enantiomer of a structure.

    Draw a diastereomer of a structure.

    September 24

    Finish Chapter 4: Stereochemistry

    September 26

    Chapter 5: Acids and Bases

    5.1 Brønsted–Lowry Acids and Bases

    5.2 Reactions of Brønsted–Lowry Acids and Bases

    5.3 Acid Strength and pKa

    5.4 Predicting the Outcome of Acid–Base Reactions

    Read sections 5.1-5.4

    OCA 3

    R/S Stereochemistry

    Assigned September 26

    Due October 3

    Reflection Due October 5

    State approximate pKa’s of organic functional groups.

    Draw conjugate acids and bases for a reaction given acid/base reactants.

    Determine the direction an acid base reaction will proceed.

    September 28

    Chapter 5: Acids and Bases

    5.5 Factors That Determine Acid Strength

    5.6 Common Acids and Bases

    5.7 Lewis Acids and Bases

    Read sections 5.5-5.7

    Explain structural effects on acidity, including element, resonance and hybrid orbital effects.

    Categorize molecules as Lewis acids vs. Lewis bases.

    Draw simple Lewis acid-base interactions to form complexes or intermediates.

    October 1

    Finish Chapter 5: Acids and Bases

    October 3

    Chapter 6: Understanding Organic Reactions

    6.1 Writing Equations for Organic Reactions

    6.2 Kinds of Organic Reactions

    6.3 Bond Breaking and Bond Making

    6.4 Thermodynamics

    6.5 Enthalpy and Entropy

    6.6 Reaction Coordinate Diagrams

    Read sections 6.1-6.6

    OCA 4

    Mechanisms and EPF

    Assigned October 3

    Due October 17

    Reflection Due October 19

    Use the common symbols to describe chemical reactions.

    Sketch reaction coordinate diagrams for concerted reactions.

    October 5

    Chapter 6: Understanding Organic Reactions

    6.7 Reaction Coordinate Diagram for a Two-

    Step Reaction Mechanism

    6.8 Kinetics

    6.9 Catalysts

    6.10 Enzymes

    Read sections 6.7-6.10

    Sketch reaction coordinate diagrams for concerted and stepwise reactions, incorporating activation energy and Gibbs Free Energy.

    Write rate laws for concerted and stepwise reactions.

    Explain how rate laws can be used to determine viable reaction mechanisms.

    Illustrate how catalysts affect reaction coordinate diagrams.

    Explain how reaction coordinate diagrams relate to activation energy, mechanism and Gibbs Free Energy.

    October 8

    Finish Chapter 6: Understanding Organic Reactions

    October 10

    Exam 2 Chapters 4-6

    October 12

    Chapter 7: Alkyl Halides and Nucleophilic Substitution

    7.1 Introduction to Alkyl Halides

    7.2 Nomenclature

    7.3 Physical Properties

    7.4 Interesting Alkyl Halides

    7.5 The Polar Carbon–Halogen Bond

    7.6 General Features of Nucleophilic Substitution

    7.7 The Leaving Group

    7.8 The Nucleophile

    7.9 Possible Mechanisms for Nucleophilic Substitution

    7.10 Two Mechanisms for Nucleophilic Substitution

    Read sections 7.1-7.10

    Identify alkyl halides as primary, secondary or tertiary.

    Identify solvents as nonpolar, polar aprotic or polar protic.

    Discuss stability of carbocations based on their substitution.

    Explain what makes a strong nucleophile.

    Explain solvation of nucleophiles by polar protic solvents.

    October 15

    Chapter 7: Alkyl Halides and Nucleophilic Substitution

    7.11 The SN2 Mechanism

    7.12 Application: Useful SN2 Reactions

    7.13 The SN1 Mechanism

    7.14 Carbocation Stability

    7.15 The Hammond Postulate

    7.16 Application: SN1 Reactions, Nitrosamines, and Cancer

    7.17 When Is the Mechanism SN1 or SN2?

    Read sections 7.11-7.17

    Explain steric effects and how they relate to SN1 and SN2 mechanisms.

    Differentiate between SN1 and SN2 mechanisms.

    Draw accurate SN1 mechanisms.

    Draw accurate SN2 mechanisms.

    Describe the stereochemical outcome of SN1 and SN2 mechanisms.

    Determine rate laws for SN1 and SN2 mechanisms.

    October 17

    Continue Chapter 7: Alkyl Halides and Nucleophilic Substitution

    OCA 5

    Reaction Coordinate Diagrams

    Assigned October 17

    Due October 24

    Reflection Dues October 26

    October 19

    Fall Break – No Class

    October 22

    Finish Chapter 7: Alkyl Halides and Nucleophilic Substitution

    October 24

    Chapter 8: Alkyl Halides and Elimination Reactions

    8.1 General Features of Elimination

    8.2 Alkenes—The Products of Elimination Reactions

    8.3 The Mechanisms of Elimination

    8.4 The E2 Mechanism

    8.5 The Zaitsev Rule

    Read sections 8.1-8.5

    OCA 6

    Elimination reactions and Acyl addition

    Assigned October 24

    Due October 31

    Reflection Due November 2

    Discuss stability of alkenes based on substitution.

    Incorporate Zaitsev’s rule to determine elimination products.

    Explain how base strength and solvent affect elimination mechanisms.

    Draw accurate E2 mechanisms.

    October 26

    Dr. Morsch Away – no class

    October 29

    Chapter 8: Alkyl Halides and Elimination Reactions

    8.6 The E1 Mechanism

    8.7 SN1 and E1 Reactions

    8.8 Stereochemistry of the E2 Reaction

    8.9 When is the Mechanism E1 or E2

    8.10 E2 Reactions and Alkyne Synthesis

    8.11 When Is the Reaction SN1, SN2, E1, or E2?

    Read sections 8.1-8.5

    Draw accurate E1 mechanisms.

    Differentiate between E1 and E2 mechanisms.

    Differentiate between SN1, SN2, E1 and E2 mechanisms, including the possibility of having more than one mechanism occurring.

    October 31

    Finish Chapter 8: Alkyl Halides and Elimination Reactions

    November 2

    Chapter 9: Alcohols, Ethers and Epoxides

    9.1 Introduction

    9.2 Structure and Bonding

    9.3 Nomenclature

    9.4 Physical Properties

    9.5 Interesting Alcohols, Ethers, and Epoxides

    9.6 Preparation of Alcohols, Ethers, and Epoxides

    9.7 General Features—Reactions of Alcohols,

    Ethers, and Epoxides

    9.8 Dehydration of Alcohols to Alkenes

    Read sections 9.1-9.4, 9.6-9.8

    OCA 7

    Mechanism description with partner feedback

    Assigned October 31

    Due Nov 14

    Identify primary, secondary and tertiary alcohols.

    Draw elimination mechanisms with sulfuric acid or with phosphorus oxychloride and excess pyridine.

    November 5

    Chapter 9: Alcohols, Ethers and Epoxides

    9.9 Carbocation Rearrangements

    9.10 Dehydration Using (POCl3) and Pyridine

    9.11 Conversion of Alcohols to Alkyl Halides with HX

    9.12 Conversion of Alcohols to Alkyl Halides with SOCl2 and PBr3

    9.13 Tosylate—Another Good Leaving Group

    9.14 Reaction of Ethers with Strong Acid

    9.15 Reactions of Epoxides

    Read sections 9.9-9.15

    Draw halogenation mechanisms with hydrochloric acid, thionyl chloride and pyridine, or phosphorus tribromide and pyridine.

    Draw mechanism for conversion of alcohols to tosylates (tolunesulfonates).

    Draw reaction of tosylates with nucleophiles.

    Draw mechanism of ethers reacting with strong halogen acids.

    Draw mechanism of epoxides reacting with nucleophiles.

    November 7

    Chapter 9 ARC activity

    November 9

    Continue Chapter 9: Alcohols, Ethers and Epoxides

    November 12

    Exam 3 Chapters 7-9

    November 14

    Chapter 10 & 11: Alkenes and Alkynes

    10.1 Introduction

    10.2 Calculating Degrees of Unsaturation

    10.3 Nomenclature

    10.4 Physical Properties

    10.7 Preparation of Alkenes

    10.8 Introduction to Addition Reactions

    10.9 Hydrohalogenation—Electrophilic Addition of HX

    10.10 Markovnikov’s Rule

    10.11 Stereochemistry of Electrophilic Addition of HX

    10.12 Hydration—Electrophilic Addition of Water

    10.13 Halogenation—Addition of Halogen

    10.14 Stereochemistry of Halogenation

    Read sections 10.1-10.14

    Final Reflection

    Assigned November 14

    Due November 21

    Name alkenes and alkynes using IUPAC nomenclature.

    Draw previous elimination reaction mechanisms that form alkenes and alkynes from alkyl halides or alcohols.

    Draw electrophilic addition mechanism for reactions with acid/water and with HX.

    Show proper regiochemistry of electrophilic addition based on Markovnikov’s rule.

    Draw mechanism for halogenation, using halonium intermediate to explain stereochemistry.

    November 16

    Chapter 10 & 11: Alkenes and Alkynes

    10.15 Halohydrin Formation

    10.16 Hydroboration–Oxidation

    11.1 Introduction

    11.2 Nomenclature

    11.3 Physical Properties

    11.4 Interesting Alkynes

    11.5 Preparation of Alkynes

    11.6 Introduction to Alkyne Reactions

    11.7 Addition of Hydrogen Halides

    Read sections 10.15-10.16

    Read sections 11.1-11.7

    Explain how hydroboration/oxidation leads to anti-Markovnikov addition.

    Explain hydration reactions of alkynes using keto-enol tautomers to show products with carbonyl groups.

    Explain formation of acetylide ions based on pKa.

    Draw mechanisms of acetylide addition to electrophiles.

    Solve synthesis problems using any reactions from chapters 7-11.

    November 19

    Finish Chapter 10 & 11: Alkenes and Alkynes

    November 21

    Chapter 12: Oxidation and Reduction

    12.1 Introduction

    12.2 Reducing Agents

    12.3 Reduction of Alkenes

    12.5 Reduction of Alkynes

    12.6 The Reduction of Polar C–X σ Bonds

    Read sections 12.1-12.6

    Identify examples of oxidation and reduction in organic chemistry.

    Differentiate between oxidizing and reducing agents.

    Explain reduction of alkenes and alkynes using hydrogen with palladium on carbon, hydrogen/Lindlar’s Catalyst and sodium with liquid ammonia.

    Draw mechanism for reduction with lithium aluminum hydride.

    November 23

    Thanksgiving Break

    November 26

    Chapter 12: : Oxidation and Reduction

    12.7 Oxidizing Agents

    12.8 Epoxidation

    12.9 Dihydroxylation

    12.10 Oxidative Cleavage of Alkenes

    12.11 Oxidative Cleavage of Alkynes

    12.12 Oxidation of Alcohols

    Read sections 12.9- 12.12

    Draw products of epoxidation reactions, showing appropriate stereochemistry.

    Draw products of dihydroxylation reaction, explaining stereochemical outcome of reactions.

    Draw products of oxidative cleavage of alkenes and alkynes with ozone.

    Draw oxidation products of alcohols, differentiating between chromic acid and pyridinium chlorochromate in the oxidation level of the product.

    November 28

    Finish Chapter 12: Oxidation and Reduction

    November 30

    Exam 4 (Chapters 10-12)

    December 3

    Chapter 13: Aromaticity

    13.1 Background of Aromaticity

    13.2 The Structure of Benzene

    13.3 Nomenclature of Benzene Derivatives

    13.4 Spectroscopic Properties of Aromatic Compounds

    13.5 Interesting Aromatic Compounds

    13.6 Benzene’s Unusual Stability

    Read sections 13.1-13.6

    Explain how heats of hydrogenation can be used to show the special stability of aromatic compounds.

    Determine if given structures should be aromatic or not.

    December 5

    Chapter 13: Aromaticity

    13.7 The Criteria for Aromaticity—Hückel’s Rule

    13.8 Examples of Aromatic Compounds

    13.9 What Is the Basis of Hückel’s Rule?

    Read sections 13.7-13.9

    Draw molecular orbital diagrams for simple aromatic and anti-aromatic molecules (including nodes, orbital phase, bonding and anti-bonding interactions and which orbitals have electrons).

    December 7

    Review for final

    December 12

    FINAL EXAM 8-11 AM Wednesday

    This page titled Readings is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by Layne Morsch.

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