CLC Chemistry Resources

DISCLAIMER: These handouts provide a “general” outline of the material with practice problems and answers. Four students working on a whiteboardThe instructor may present the material differently, so not all of the material in the handouts maybe covered by each instructor, and some instructors may cover material not on the handouts. In addition, instructors may present the content differently; if that occurs, always follow your instructor’s preferred content. Please review your lecture notes, slides, and online text, and compare them to the handouts to note appropriate topics to work through. The material for the introductory courses (103 and 104) is gradually uploaded during the semester; the material for the organic courses (343 and 345) is available all at once.

If you find an error or have a comment on the handouts feel free to reach out to Tony Jacob at atjacob@wisc.edu. Please direct chemistry questions to Piazza or your TA.

If you wish to provide feedback, there are links available for the organic resources all the time; for the introductory chemistry courses a link near the end of the semester will be provided. We always appreciate feedback so thank you in advance!

Here’s another useful tool: A semester calendar for fall 2022! That way you can add all your assignments for each class in the boxes using a different colored pen for each course.

This is an accordion element with a series of buttons that open and close related content panels.

Chemistry 103

Tony’s Help Sheets – Chemistry 103

Instructors may present content differently than in these resources;
if that occurs, always follow your instructor’s preferred content.


Intro to Chemistry Concepts
Help Sheet #1
Intro
Terms, SI units, Unit Conversions, Sig Figs, Density, Periodic Table
Flashcards #1
SI Units
Confirm which SI units you are expected to know in your course; print 2-sided with Adobe Reader for proper alignment
Practice Sheet #1
SI Units
Conversions with SI Units
Flashcards #2
Element Names and Symbols
first 36 elements plus a few other common ones; print 2-sided with Adobe Reader for proper alignment
Practice Sheet #2
Element Names and Symbols
Help Sheet #2
Atomic Structure
Atomic Structure, Isotopes, Average Atomic Mass, Mass Spectroscopy, Ionic versus Molecular compounds, Naming/Writing Formulas, Polyatomic Ions, Coulomb’s Law
Flashcards #3
Polyatomic Ions Formulas/Names
Confirm which polyatomic ions you are expected to know in your course;
print 2-sided from Adobe Reader for proper alignment
Practice Sheet #3
Monoatomic and Polyatomic Ions
Practice Sheet #4
Naming Compounds, Writing Formulas
Chemical Reactions
Help Sheet #3
Reactions
Balancing Rxns, Types of Rxns, Writing Rxns (molecular, complete ionic, net ionic rxns); Electrolytes; Solubility Rules; Redox: Assigning oxidation numbers; What’s oxidized, reduced, oxidizing agent, reducing agent; Metal activity series
Stoichiometry (Part I)
Help Sheet #4
Stoichiometry (Part I)
Mole calculations, Molar mass, Converting between moles/grams/molecules, Mass percent, Empirical and Molecular formulas, Finding unknown metal M
Help Sheet #5
Stoichiometry (Part II)
Reactions and mol calculations, Limiting reagents, Percent yield, Empirical formulas from combustion
Practice Problems for Modules 1-4:
Intro to Chemistry Concepts; Atoms, Molecules, and Ions;
Chemical Reactions; Stoichiometry (Part I)

A set of practice problems on these modules

Stoichiometry (Part II)
Help Sheet #6
Stoichiometry (Part III)
Molarity calculations, Dilution, Solution stoichiometry (titrations); Intro to energy
11/6/22: Error on Question 10 corrected
Gases
Help Sheet #7
Gases (Part I)
Gas Laws, D and molar mass, STP, Stoichiometry with gases
Help Sheet #8
Gases (Part II)
Partial Pressure, Kinetic Theory of Gases, Root Mean Square Velocity, Diffusion and Effusion
Thermochemistry
Help Sheet #9
Thermochemistry (Part I)
Terms; Work; Sign Conventions; Specific Heat Capacity; q = CmΔT; Heat Transfer; Enthalpy of a rxn, ΔHrxn°
Help Sheet #10
Thermochemistry (Part II)
Calorimetry; Phase Changes (ΔHvap°, ΔHfus°) and heating curves; Phase Change + Heat transfer; Hess’s Law; Heat of Formation (ΔHf°)
Light, Matter, and Atomic Structure (Part I)
Help Sheet #11
Light, Matter, Atomic Structure (Part I)
Light equations; Electromagnetic spectrum; Photoelectric effect; Quantized system and Bohr Model; Energy Level Diagram; Electron Transitions; Duality principle; de Broglie Wavelength
Help Sheet #12
Light, Matter, Atomic Structure (Part II)
Quantum: Wavefunctions; Nodes; Quantum Numbers; Orbitals Shapes; Electronic Configurations: Shorthand notation; Orbital Box Diagram; Charged Transition Elements; Number of unpaired electrons

Practice Problems for Stoichiometry (Part II)
Practice Problems for Gases
Practice Problems for Thermochemistry
Practice Problems for Light, Matter, and Atomic Structure
Sets of practice problems for these modules

Light, Matter, and Atomic Structure (Part II)
Help Sheet #13
Light, Matter, Atomic Structure (Part III)
Periodic Table Trends: Effective Nuclear Charge; Shielding; Atomic Radii, Ionization Energy, Electron Affinity; Ionic Radii
Chemical Bonding
Help Sheet #14
Chemical Bonding
Types of bonds; Electronegativity; Bond polarity; Lewis dot structures; Resonance; Bond order; Formal charge; Bond enthalpies
Molecular Geometry
Help Sheet #15
Molecular Geometry (Part I)
Valence Shell Electron Pair Repulsion (VSEPR); Molecular Polarity
Help Sheet #16
Molecular Geometry (Part II)
Valence Bond Theory: Hybrid Orbitals, σ and π Bonds; Geometric isomers cis/trans
Help Sheet #17
Molecular Geometry (Part III)
Not all lecture sections are covering this topic; SKIP this HelpSheet if your lecture is not doing MO Theory!
Molecular Orbital (MO) Theory: MO Shapes; Bond order; MO e Configuration; Molecular stability
Intermolecular Forces
Help Sheet #18
Intermolecular Forces
Liquids: Intermolecular forces; Liquid properties; Vapor pressure diagram

Practice Problems for Light, Matter, and Atomic Structure (Part II)
Practice Problems for Chemical Bonding
Practice Problems for Molecular Geometry
Practice Problems for Intermolecular Forces
Sets of practice problems for these modules
More materials posted throughout the semester . . .


Chemistry 104

Tony’s Help Sheets – Chemistry 104

Instructors may present content differently than in these resources;
if that occurs, always follow your instructor’s preferred content.


Chem 103 Review
Help Sheet #1
Chem 103 Review
Electronegativity, Lewis Dot Structures, Bond Polarity, VSEPR, Hybridization, Hybrid Orbitals used in a Bond, Intermolecular Forces, Higher Boiling Point, Solubility
Organic Chemistry
Help Sheet #2
Organic (Part I)

Drawing and Naming Molecules, Functional Groups (Part I)
Practice Sheet #1
ID Functional Groups; Naming Molecules

Organic: alkanes, alkenes, alkynes, cyclic, aromatic
Help Sheet #3
Organic (Part II)

Isomers: Constitutional (also called structural); Stereoisomers: Geometric, Optical
Practice Sheet #2
Isomers
Help Sheet #4
Organic (Part III)

Functional Groups (Part II); drawing and naming
Practice Sheet #3
ID Functional Groups; Naming Molecules

Organic: alcohols, ethers, aldehydes, ketones, carboxylic acids, esters, amides, amines
Flashcards #1 – ID Functional Groups
Identifying Functional Groups
Print 2-sided with Adobe Reader for proper alignment
Help Sheet #5
Organic (Part IV)

Reactions: Ester and amide formation, ester and amide hydrolysis; Complete hydrolysis
Practice Sheet #4
Organic Reactions: Ester/amide condensation, ester/amide hydrolysis
Chemical Kinetics
Help Sheet #6
Kinetics (Part I)
Average Rates; Initial Rates; Relative Rates; Rate Constant with Units; Evaluating a Rate Law: Initial Rates Method, Description
Help Sheet #7
Kinetics (Part II)
Evaluating a Rate Law: Integrated Rate Laws; Half Life and Half life graphs; Rate versus Concentration
Help Sheet #8
Kinetics (Part III)
Evaluating a Rate Law: Mechanisms; Reaction Coordinate Diagrams; Arrhenius Equation and Graphs
Practice Problems for Organic
Practice Problems for Kinetics

Sets of practice problems for these two modules

Equilibrium
Help Sheet #9
Equilibrium (Part I)
K Expression; Size of K; Kc versus Kp; Le Chatelier’s Principle; How K Changes as Reaction is Changed
Help Sheet #10
Equilibrium (Part II)
Equilibrium Calculations; Reaction Quotient: Q; Phase Diagrams
Acids and Bases
Help Sheet #11
Acids and Bases (Part I)
Definitions; Conjugate A/B; Amphiprotic; Ka, Kb; Strength of A/B and Their Conjugates; Which Way does an A/B Rxn Proceed; Acidity versus Structure
Help Sheet #12
Acids and Bases (Part II)
Autoionization; pH Equations; pH Calculations for SA, SB, WA, and WB; %Ionization; Ka, Kb, pKa, pKb; Which Way does an A/B Rxn Proceed (re-visited); Polyprotic Acids; Lewis acids/bases; Spectator Ions; Salts
Practice Problems for Equilibrium
Practice Problems for Acids & Bases

Sets of practice problems for these two modules

Aqueous Equilibria
Help Sheet #13
Aqueous Equilibria (Part I): Buffers
ID Buffers; pH of a Buffer; Find pH of Buffer After Adding SA/SB; Buffer Range; Buffer Capacity; Buffer Preparation
Help Sheet #14
Aqueous Equilibria (Part II): Titrations
Titration Curves: Strong Acid+Strong Base, Strong Acid+Weak Base, Weak Acid+Strong Base; Equivalence Point; Halfway to Equivalence Point; Indicators; pH Calculations of Titrations; Polyprotic Acid Titrations
Help Sheet #15
Aqueous Equilibria (Part III): Solubility
Find Ksp from Solubility; Find Solubility from Ksp; Which Solid is More Soluble?; Common Ion Effect; pH and Solubility; Does a Ppt Form?
Thermodynamics
Help Sheet #16
Thermodynamics (Part I)
Spontaneity; Entropy, ΔS°; Pascal’s Triangle; Comparing Entropy Qualitatively; ΔSuniv°; T of a phase change; Enthalpy, ΔH° (review); Laws of Thermodynamics
Help Sheet #17
Thermodynamics (Part II)
Free Energy, ΔG°; Deriving ΔG°; ΔGf°; Signs of ΔH°, ΔS°, and ΔG°: Reaction spontaneity; T at which a reaction is spontaneous; Free Energy ΔG under non-standard conditions; G vs Extent of Reaction; Van’t Hoff equation and graph; Thermodynamics versus Kinetics
Practice Problems for Aqueous Equilibria
Practice Problems for Thermodynamics (Part I)

Sets of practice problems for these two modules
Electrochemistry
Help Sheet #18
Electrochemistry (Part I)
Assign Oxidation Numbers; Oxidized, reduced, oxidizing/reducing agents; Balance Redox Reations; Draw Electrochemical Cells and label parts; Inert Electrodes; Line Notation; Standard Hydrogen Electrode (SHE); How E° Changes as Reaction Changes; Standard Reduction Table
More materials posted throughout the semester . . .


Chemistry 343

José’s Chemistry 343 Resources

Instructors may present content differently than in these resources;
if that occurs, always follow your instructor’s preferred content.


*** Using these Chem 343 handouts? Your FEEDBACK would be really appreciated! Thanks in advance! ***
Please note that these Chem 343 materials require a UW NetID and Password

#1: Lewis Structures (answers) #2: Resonance Structures (answers) #3: Electron Pushing Arrows in O-Chem
#4: Alkane Nomenclature (answers) #5: Lewis Acids and Bases (answers) #6: Acid Base Practice Problems (answers)
Reactions of Alkenes-Flashcard Format
#1: Overview: Alkene Addition Reactions #2: Hydrogenation #3: Halogenation
#4: Hydration of Alkenes; Synthesis of Alcohols #5: Halohydrin Synthesis #6: Haloether Synthesis
#7: Oxymercuration-Reduction #8: Alkoxymercuration-Reduction #9: Hydroboration-oxidation
#10: Ozonolysis #11: Addition of HBr in the Presence of Peroxides #12: 1,2-Diol Formation #1
#13: 1,2-Diol Formation #2 #14: Alkene Isomerization
Addition Reactions to Alkenes Practice
Practice #1: Addition Reactions to Alkenes (answers)
Practice #2: Addition Reactions to Alkenes (answers)
Practice on Stereoisomers
Practice #3: Stereoisomers (answers)
Practice on Cyclohexanes
Practice #4: Cyclohexanes (answers)
Substitution (SN1 and SN2) and Elimination (E1 and E2) Reactions
Trends in Alkyl Substitution and Elimination Reactions
Practice #5: SN1, SN2 (answers)
Practice #6: Practice Questions (Mainly multiple-choice questions) (answers)
Practice #7: Practice Problems on Synthesis (answers)
Carbenes and Carbenoids-Flashcard Format
#1: Carbene and Carbenoid Reactivity
Halogenation of Alkanes-Flashcard Format
#1: Halogenation of Alkanes
Organometallics-Flashcard Format
#1: Organometallic Compounds
Alcohol Reactions-Flashcard Format
#1: Alkyl Chlorides from 1o and 2o Alcohols #2: Alkyl Bromides from 1o and 2o Alcohols #3: Alkyl Halides from 3o Alcohols
#4: Sulfonate Ester Preparation #5: Ethers from Alcohols Using Sulfonates #6: Oxidation of 1o Alcohols to Aldehydes
#7: Oxidation of 1o Alcohols to Carboxylic Acids #8: Oxidation of 2o Alcohols to Ketones #9: Rxn of 1o Alcohols with Hydrogen Halides
#10: Rxn of 2o Alcohols with Hydrogen Halides #11: Rxn of 3o Alcohols with Hydrogen Halides #12: Acid Catalyzed Dehydration of an Alcohol
Reactions of Ethers-Flashcard Format
#1: Ethers from 1o Alcohols #2: Ethers from 3o Alcohols #3: Williamson Ether Synthesis
#4: Ethers from Alkenes; Alkoxymercuration-Reduction of Alkenes #5: Rxn of Ethers with HX (1 equivalent) #6: Rxn of Ethers with Excess HX
Reactions of Epoxides-Flashcard Format
#1: Synthesis of Epoxides Using Peroxides #2: Synthesis of Epoxides Using Halohydrins #3: Acid Catalyzed Nucleophilic Reaction of an Epoxide
#4: Base-Catalyzed Nucleophilic Reaction of an Epoxide #5: Reactions of Epoxide With Organometallics
Practice on Epoxides
Practice #8: Practice Problems on Epoxide Reactivity (answers)
Synthesis and Reactions of Alkynes-Flashcard Format
#1: Synthesis of Alkynes #2: Hydrogenation of Alkynes #3: Partial Hydrogenation of Alkynes-I
#4: Partial Hydrogenation of Alkynes-II #5: Addition of 1 equivalent of HX to Alkynes #6: Addition of Excess HX to Alkynes
#7: Addition of HX in the Presence of Peroxides #8: Hydration of Alkynes #9: Hydroboration-Oxidation of Terminal Alkynes
#10: Hydroboration-Oxidation of Internal Alkynes
Alkyne Practice
Practice #9: Alkyne Reactions (answers)
Synthesis
Practice #10: Synthesis Practice (answers)
Dienes-Flashcard Format
#1: Electrophilic Addition to 1,3-Conjugated Dienes
Diels-Alder-Flashcard Format
#1: Diels-Alder Reaction
Diels-Alder Practice
Practice #11: Practice on the Diels-Alder Reaction (answers)

*** Using these Chem 343 handouts? Your FEEDBACK would be really appreciated! Thanks in advance! ***


Chemistry 345

José’s Chemistry 345 Resources

Instructors may present content differently than in these resources;
if that occurs, always follow your instructor’s preferred content.


*** Using these Chem 345 handouts? Your FEEDBACK would be really appreciated! Thanks in advance! ***
Please note that these Chem 345 materials require a UW NetID and Password

1H NMR
#1: 1H NMR Spectroscopy Worksheet (answers) #2: Strategies for Solving Problems using 1H NMR, IR
IR Spectroscopy
#1: Practice Problems Ion IR Spectroscopy
(answers)
#2: More Practice Problems on IR Spectroscopy
(answers)
Electron Pushing Arrows
#1: Electron Pushing Arrows in O-Chem
Electrophilic Aromatic Substitution (EAS) – Flashcard Format
#1: EAS Nitration #2: EAS Bromination #3: EAS Chlorination
#4: EAS Sulfonation #5: EAS Friedel-Crafts Alkylation #6: EAS Friedel-Crafts Acylation
Practice #1: EAS Reactions (answers)
Benzylic and Allylic Reactions – Flashcard Format
#1: Allylic Bromination #2: Benzylic Bromination #3: Synthesis of Allylic Grignard Reagents
#4: Substitution Reactions #5: Elimination Reactions #6: Oxidation Reaction of Allylic and Benzylic Alcohols
Oxidation of Alkylbenzenes – Flashcard Format
#1: Oxidation of Alkylbenzene Compounds
Elimination Reactions of Vinyl Halides – Flashcard Format
#1: Alkyne Synthesis
Nucleophilic Aromatic Substitution – Flashcard Format
#1: Nucleophilic Aromatic Substitution
Reactions of Phenols – Flashcard Format
#1: Phenol Reactivity Toward Electrophilic Aromatic Substitution (EAS) #2: Reaction of Aryl Alkyl Halides with HX #3: Oxidation of Phenols
#4: Williamson Ether Synthesis
Reactions Involving Transition Metal Complexes – Flashcard Format
#1: The Heck Reaction #2: Suzuki Coupling Reaction #3: Olefin Metathesis Reaction
Aldehyde and Ketone Reactivity – Flashcard Format
#1: Aldehyde and Ketone Reduction #2: Cyanohydrin Synthesis #3: Reaction With Grignard Reagents
#4: Reaction With Acetylide Reagents #5: Acetals #6: The Base Catalyzed Formation of a Hemiacetal
#7: The Wolff-Kishner Reduction #8: The Clemmensen Reduction #9: Reaction With Primary Amines
#10: Reaction With Secondary Amines #11: The Wittig Reaction #12: The Baeyer-Villiger Reaction
#13: The Beckmann Rearrangement Reaction
Practice #2: Problems on Acetals and Synthesis (answers)
Reactivity of Carboxylic Acids and Their Derivatives – Flashcard Format
#1: Synthesis of Carboxylic Acids #2: Synthesis of Esters From Carboxylates #3: Methyl Esters by the Use of Diazomethane
#4: Fischer Esterification #5: Acid Chlorides from Carboxylic Acids #6: Transesterification
#7: Reduction of Carboxylic Acids to 1o-alcohols #8: Synthesis of Acid Anhydrides #9: Synthesis of Sulfonyl Chlorides
#10: Decarboxylation of β-Dicarboxylic Acids #11: Base Catalyzed Hydrolysis of an Amide #12: Acid Catalyzed Hydrolysis of an Amide
#13: Reaction of Esters With Grignard Reagents #14: Reaction of an Acid Chloride with a Lithium Dialkylcuprate #15: Reaction of Esters With Amines to Form Amides
#16: Hydrolysis of Acid Chlorides #17: Hydrolysis of Acid Anhydrides
#19: Base Catalyzed Lactone Hydrolysis #20: Base Catalyzed Hydrolysis of Nitriles #21: Acid Catalyzed Hydrolysis of Nitriles
#22: Acid Chloride Reactions #23: Acid Catalyzed Hydrolysis of Lactones #24: Acid Catalyzed Hydrolysis of Esters
#25: Reduction of Derivatives of Carboxylic Acid #26: Reduction of Acid Chlorides to Aldehydes #27: The Strecker Synthesis
#28: Reaction of Nitriles With Grignard Reagents
Practice #3: Problems on Carboxylic Acids and Synthesis (answers)
Reactivity of Enols, Enolate Ions and α,β-Unsaturated Carbonyl Compounds – Flashcard Format
#1: Formation of Enols Under Acidic Conditions #2: Formation of Enolate Ions Under Basic Conditions #3: The α-Halogenation of Carbonyl Compounds
#4: The Haloform Reaction #5: The Aldol Reaction Under Acidic Conditions #6: The Aldol Reaction Under Basic Conditions
#7: Halogenation of Carboxylic Acids #8: α, β-Conjugate Addition Reaction (Michael Addition) #9: 1,2 vs 1,4 Addition Reactions to α, β-Conjugate Carbonyl Compounds
#10: Claisen Condensation and Other Similar Reactions #11: The Robinson Annulation Reaction
Reactivity of Amine Compounds – Flashcard Format
#1: Direct Alkylation of Amines #2: Reactions of Amines: Acylation #3: Primary Amine Derivatives of Aldehydes and Ketones
#4: Secondary Amine Derivatives of Aldehydes and Ketones #5: Reactions of Amines: Reductive Amination (Borch Reaction) #6: Synthesis of Primary Amines (Gabriel Synthesis)
#7: Synthesis of Arylamines #8: Quaternization of Amines #9: Hofmann Elimination
#10: Electrophilic Aromatic Substitution (EAS) of Arylamines #11: Aromatic Substitution With Diazonium Salts #12: Reactions of Amines: Diazonium Salts
#13: Buchwald-Hartwig Amination #14: Curtius Rearrangement #15: Hofmann Rearrangement
#16: The Sandmeyer Reaction #17: The Mannich Reaction

*** Using these Chem 345 handouts? Your FEEDBACK would be really appreciated! Thanks in advance! ***