Readings

Last updated
Save as PDF

Page ID: 25275

\( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\)

Organic Chemistry I – CHE 267 FALL 2018 Course Schedule

Class Day	Topic	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 Day – No 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 S_N2 Mechanism 7.12 Application: Useful S_N2 Reactions 7.13 The S_N1 Mechanism 7.14 Carbocation Stability 7.15 The Hammond Postulate 7.16 Application: S_N1 Reactions, Nitrosamines, and Cancer 7.17 When Is the Mechanism S_N1 or S_N2? Read sections 7.11-7.17		Explain steric effects and how they relate to S_N1 and S_N2 mechanisms. Differentiate between S_N1 and S_N2 mechanisms. Draw accurate S_N1 mechanisms. Draw accurate S_N2 mechanisms. Describe the stereochemical outcome of S_N1 and S_N2 mechanisms. Determine rate laws for S_N1 and S_N2 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 S_N1, S_N2, 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

Organic Chemistry I – CHE 267 FALL 2018 Course Schedule

Class Day

Topic

Skype Assignments

Learning Objectives