INTRO TO ORGANIC CHEMISTRY COURSE
This is the course page for Introduction to Organic Chemistry. Here you will find the details of the course, listed by Topic (1-6) and in turn by the sub-headings of Notes, Homework, Tests, Quizzes and Other. This page should help you to keep track of the progression of the course throughout the semester.
TOPIC 1 – Nomenclature
Notes:
Homework:
- Organic Worksheet 01a
- Organic Worksheets 01b, 01c, 01d
- Review for Quiz 01a and Test 01
Tests:
- 01 – Nomenclature
Quizzes:
- 01a – Skeletal, Graphical, Molecular and Empirical Formula conversions
Labs:
- 01a – Models & Nomenclature
Other:
MSU problems;
- MSU GQ1 – Common Valencies
- MSU GQ4 – Line & Condensed Structural Formulas
- MSU GQ5 – Identifying Line Formulas
- MSU GQ7 (1-6) – Structural Formulas & Alkane Nomenclature
- MSU GQ12 (1-4) – Interpreting Molecular Formulas of Hydrocarbons
- MSU N1 – Identifying IUPAC Suffix and Chain Length
- MSU N2 – Alkane Nomenclature
- MSU N3 – Nomenclature Problems
- MSU GQ19 – Identifying Functional Groups
- MSU GQ20 – Functional Groups I
- MSU GQ21 – Functional Groups II
Textbook (Organic Chemistry: A Short Course 13th Ed., Hart, Haddad, Craine & Hart) Reading & Problems;
- p38-44 Alkane & Halogeno Nomenclature: 2.1, 2.2, 2.3, 2.4, 2.6, 2.7, 2.8
- p50-64 Cycloalkane Nomenclature: 2.10, 2.11, 2.12, 2.26, 2.27, 2.28, 2.29, 2.30
- p72-109 Alkene and Alkyne Nomenclature: 3.3, 3.4, 3.34, 3.35 (a-e, i-j)
- p120-141 Aromatic Nomenclature: 4.7, 4.8, 4.20 (a-e, g, i, l-m), 4.21 (a-b, d, f, h)
- p208-230 Alcohol Nomenclature: 7.1, 7.2, 7.26 7.27 (a-f, i-j), 7.29
- p255-283 Aldehyde & Ketone Nomenclature: 9.1, 9.2, 9.30 (a-f, h, i), 9.31 (a-e, g, i-j)
- p289-322 Carboxylic Acid Nomenclature: 10.1, 10.2, 10.37 (a-c, i-k), 10.38
- p310 Ester Nomenclature: 10.14, 10.15
- p323 Acid Halide Nomenclature: 10.44 (i)
- p313 Amide Nomenclature: 10.31
- p329 Amine Nomenclature: 11.2, 11.3, 11.4, 11.24 (a-i, k-l), 11.25 (a-f)
Links;
- Ian Hunt’s (University of Calgary) Guide to Introductory IUPAC Organic Nomenclature
- Ian Hunt’s (University of Calgary) Guide to Basic IUPAC Organic Nomenclature
- Official ‘Blue Book’ ACD Labs/IUPAC Nomenclature
TOPIC 2 – Isomerism
Notes:
Homework:
- Organic Worksheet 02a
- Organic Worksheet 02b
- Organic Worksheet 02f
- Organic Worksheet 02e
Tests:
- 02 – Isomerism
Quizzes:
- 02a – Structural Isomerism
- 02b – Stereoisomerism
Labs:
- 02 – Cis/Trans Isomerism
Other:
MSU Problems;
- MSU FGR7 – Alkane Halogenation (possible isomers)
- MSU CS8 – Alkene E/Z notation
- MSU CS2 (Q1) – Isomer Recognition (N.B. Constitutional = Structural)
- MSU CS3 – Identifying Conformers
- MSU (A & E) – Configuration Nomenclature
- MSU CS17 (Q2, 4, 6 & 8)
Textbook (Organic Chemistry: A Short Course 13th Ed., Hart, Haddad, Craine & Hart) Reading and Problems;
- p12-64 Structural Isomerism: 1.17, 1.20, 1.38, 1.39, 2.31
- p47-49 Conformers: 2.9
- p76-78 Geometric (Cis/Trans) Isomerism: 3.6
- p148-152 Optical Isomerism: 5.2, 5.3, 5.4, 5.5
- p153-157 R-S Convention: 5.10, 5.11
- p157-158 E-Z Convention: 5.12, 5.13
Links;
- Jim Clark’s Geometric Isomerism Questions
- Jim Clark’s Geometric Isomerism Questions – Answers
- Jim Clark’s Geometric Isomerism Questions E/Z notation
- Jim Clark’s Geometric Isomerism Questions E/Z notation – Answers
- Thalidomide article C&EN
- UC Davis Thalidomide Wiki
- Butane Conformers PE
- Butane Conformers PE
- Butane Conformers with dihedral angles and PE
- Short Video Clip on Enantiomers and R/S Configuration
- 2001 Nobel Prize in Chemistry (Chirality)
TOPIC 3 – Mechanisms
Notes:
Homework:
- Organic Worksheet 03a
- Organic Worksheet 03b
- Organic Worksheet 03c
Tests:
- 03 – Mechanisms
Quizzes:
- 03a – Mechanisms and Curly Arrows
Labs:
- 03 – Lewis Acids and Bases in complex ions –
Other:
MSU Problems;
- MSU M3 (1-8) – Evaluating Curved Arrow Mechanisms Part 1
- MSU M4 (1-3) – Evaluating Curved Arrow Mechanisms Part 2
- MSU EN2 – Identifying Electrophiles
- MSU EN3 – Identifying Nucleophiles
- MSU GQ9 – Identifying Polarity in Molecules
- MSU GQ16 – Hybridization
- MSU GQ17 – Hybridization in a Single Molecule Part 1
- MSU GQ18 – Hybridization in a Single Molecule Part 2
Textbook (Organic Chemistry: A Short Course 13th Ed., Hart, Haddad, Craine & Hart) Reading & Problems;
- p59-67 Homolytic Free Radical Substitution: 2.19, 2.20, 2.21, 2.22, 2.23, 2.24, 2.25, 2.50, 2.51, 2.52
- p79-113 Heterolytic Electrophilic Addition: 3.8, 3.9, 3.10, 3.12, 3.41, 3.42, 3.62
- p142 Heterolytic Electrophilic Substitution: 4.30
- p191-203 Heterolytic Nucleophilic Substitution: 6.6 (first part), 6.8, 6.11, 6.12 (d, f, g)
Links;
- ChemDoodle Mechanism Drawing, University College Dublin, Ireland
- Electrophilic Aromatic Substitution (Video Tutorial)
- Animations of mechanisms (very helpful)
- Jim Clark’s Simple Notes on Curly Arrows
- Jim Clark’s Curly Arrow Worksheet (answers here)
- A few, simple exercises on curly arrows
- RSC – Mechanism Inspector
- RSC – Curly Arrows for the Gifted & Talented!
- The History of the Curly Arrow (Chemistry World article)
TOPIC 4 – The Reaction Catalog
Notes:
Homework:
- Review for Quizzes 04a-04d and Topic 04 Test
- Organic Worksheet 04a
Tests:
- 04 Reaction Catalog
Quizzes:
- 04a – Reactions 1-5
- 04b – Reactions 6-13
- 04c – Reactions 14-16
- 04d – Reactions 17-21
Labs:
- 04a – Preparation of Esters
- 04b – Fermentation
- 04c – Organic Smells Identification Kit (Esters etc.)
- 04d – Synthesis of Aspirin
- 04e – Polymerization 1 (Foam)
- 04f – Polymerization 2 (Slime)
- 04g – Oxidation of an aldehyde
Other:
MSU Problems;
- MSU FGR 8 (R + R =>?, All 3 reactants with HCl & Br2) – Alkene Addition Reactions (RC #7)
- MSU FGR 40 (Butanoic acid reactant with LiAlH4, SOCl2 & ethanol) – Reactions of acids (RC #5, #10, #3)
- MSU FGR 36 (Propanal, with reagents on rows 4, 5, 7, 8 & 11) – Reactions of propanal (RC #4, #15, #5, #4)
- MSU FGR 38 (R + R =>?, All 3 reactants with Jones’, NaBH4 & C6H5MgBr) – Carbonyl Reactions (RC #4, #5, #15)
- MSU FGR 41 (1st two reactants with single step LiAlH4, SOCl2, KOH, C2H5OH) – Acid reactions (RC #5, #10, #3)
- MSU FGR 42 – Carbonyl Reactions (RC #5, #3, #4)
- MSU S 1 – (All starting materials with PCC and Jones’) – Forming aldehydes & ketones (RC #4)
Textbook (Organic Chemistry: A Short Course 13th Ed., Hart, Haddad, Craine & Hart) Reading & Problems;
- RC#1: 6.1a, 6.2b
- RC#2: 6.9
- RC#3: 10.16, 10.19
- RC#4: 7.3
- RC#5
- RC#6: 2.19, 2.20, 2.21
- RC#7: 3.8, 3.9, 3.10, 3.11, 3.12, 3.13, 3.14
- RC#8: 7.14(a)
- RC#9: 7.16, 7.17
- RC#: 10.22
- RC#11: 4.30(a)
- RC#12: 4.38(g)
- RC#13: 10.42(c)
- RC#14: 6.2(c)
- RC#15: 9.14, 9.15, 10.10, 10.11
- RC#16: 10.22
- RC#17: 10.13 (one route)
- RC#18: 11.10
- RC#19: 11.17
- RC#20: None
- RC#21: None
Links;
- James Kennedy’s, Ester Aroma and Taste Infographic
- James Kennedy’s, Other Organic Compounds Aroma Infographic
- Adrian Dingle’s Beery Molecules Blog Series (6 posts)
- Ian Hunt (University of Calgary) Markovnikov Addition
- Towson University Alkane Quizzes;
TOPIC 5 – Structure Determination
Notes:
Homework:
Tests:
- None
Quizzes:
- 05a – Determining Structure
Labs:
Other:
MSU Problems;
Textbook (Organic Chemistry: A Short Course 13th Ed., Hart, Haddad, Craine & Hart) Reading & Problems;
Links;
- University of Colorado at Boulder Organic Spectroscopy Problems
- Rod Beavon Organic Problem #3 – answer is here
- Rod Beavon Organic Problem #6 – answer is here
- Rod Beavon’s Synthesis Problems (x2)
- London Linear Jan 96 Paper 2 Q4A
- Rod Beavon Organic Problem #5 – answer is here
- Rod Beavon Organic Problem #4 – answer is here
- Rod Beavon Organic Problem #7 – answer is here
TOPIC 6 – Synthesis
Notes:
Homework:
Tests:
Quizzes:
Labs:
Other:
MSU Problems;
Textbook (Organic Chemistry: A Short Course 13th Ed., Hart, Haddad, Craine & Hart) Reading & Problems;
Links;
