CLC Chemistry Resources

DISCLAIMER: These handouts provide a “general” outline of the material with practice problems and answers. Each 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. Please review your lecture recordings, 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, 104, and 109) 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 2021! That way you can add all your assignments for each class in the boxes using a different colored pen for each course.

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Chemistry 103

Tony’s Help Sheets – Chemistry 103


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
Atoms, Molecules, and Ions
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
Update (9/14/21): Corrected: Answer to Question #25
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
More to come . . .


Chemistry 104

Tony’s Help Sheets – Chemistry 104


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
More to come . . .


Chemistry 109

Tony’s Help Sheets – Chemistry 109


Review Material
Review (Part I): Help Sheet #1
Intro
Terms, Sig Figs, D, SI units, Unit Conversions, Periodic Table
Review (Part II): Help Sheet #2
Atomic Structure
Atomic Structure, Isotopes, Avg Atomic Mass, Naming/Writing Formulas, Polyatomic Ions
Review (Part III): Help Sheet #3
Stoichiometry (Part I)
Mole calculations, Molar Mass, Mass Percent, Empirical and Molecular Formulas, Finding M
Review (Part IV): Help Sheet #4
Reactions
Balancing Reactions, Electrolytes, Types of Reactions, Writing Reactions (molecular, complete ionic, net ionic), Solubility Rules, Redox: Assigning oxidation numbers; what’s oxidized, reduced, oxidizing agent, reducing agent
Review (Part V): Help Sheet #5
Stoichiometry (Part II)
Stoichiometry, Limiting Reagents, Percent Yield, Empirical Formulas from combustion
Review (Part VI): Help Sheet #6
Stoichiometry (Part III)
Molarity Calculations, Dilution, Solution Stoichiometry
Light, Electronic Structure, and Periodic Table Trends
Help Sheet #7
Light and Electronic Structure
Electromagnetic Spectrum, Interference, Light Equations, Photoelectric Effect, Quantized System and Bohr Model, Electron Equations/Transitions, de Broglie equation
Help Sheet #8
Quantum and Electron Configuration
Quantum, Wavefunctions, and Plots; Quantum Numbers, Nodes, Orbitals Shapes, Electron Configurations: Shorthand Notation, Orbital Energy Diagram, Charged Elements, Hund’s Rule, Charged Transition Metals, Unpaired Electrons
Help Sheet #9
Periodic Table Trends
Effective Nuclear Charge, Shielding, Periodic Table Trends: Atomic Radii, Ionization Energy, Electron Affinity, Ionic Radii; Coulomb’s Law
Chemical Bonding
Help Sheet #10
Chemical Bonding (Part I)
Molecular Orbital (MO) Theory: MO Shapes; Bond order; MO e Configuration; Molecular stability
Help Sheet #11
Chemical Bonding (Part II)
Lewis dot structures, Resonance, Bond order, Bond enthalpies, Formal charge
Help Sheet #12
Organic (Part I)

Functional Groups (Part I), Drawing molecules, Addition reactions (if covered), Naming molecules, Geometric isomers (if covered)
More to come . . .


Chemistry 343

José’s Chemistry 343 Resources


*** 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
#3: Practice: Stereoisomers (answers)
Practice on Cyclohexanes
#4: Practice: 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


*** 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</A
#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: Alkene 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! ***