| Fall 2025 | Coll of Sci, Engr & Tech | Chemistry & Biochemistry | CHEM-2310 | Organic Chemistry I | 2 | • Organic Chemistry: A Tenth Edition, John McMurry • https://openstax.org/details/books/organic-chemistry • Digital: ISBN-13: 978-1-951693-98-5 • License: by OpenStax is licensed under Creative Commons Attribution-NonCommercial-ShareAlike License v4.0 | • Preparing for Your ACS Examination in Organic Chemistry: The Official Guide. ISBN 978-1-7327764-1-8 | 12.5 % Exam 1 10 % Quizzes
12.5 % Exam 2 10 % Homework Journals and Reflections
12.5 % Exam 3 5 % Daily Attendance and Impromptu Assignments
12.5 % Exam 4 5 % In class presentation/problems
20 % Final Exam 100 % TOTAL
| 1. Welcome and Syllabus Overview
Overview of course expectations, grading, and the foundational role of organic chemistry.
2. Atomic Structure and Bonding
Review atomic structure, Lewis diagrams, and the basics of bonding in organic molecules.
3. Hybridization and Molecular Geometry
Explore sp³, sp², and sp hybridization and how they influence molecular shapes.
4. Molecular Orbitals and Bond Angles
Learn to relate hybrid orbitals and bonding to predicted bond angles.
5. Quiz 1, in class
Quiz on bonding and hybridization, followed by in-class review of concepts and errors.
6. Polarity and Formal Charges
Assign dipoles and formal charges to identify reactive regions in molecules.
7. Resonance Structures
Draw resonance forms using curved arrows and identify major contributors.
8. Resonance Practice
Apply resonance principles to common organic ions and delocalized systems.
9. Acids and Bases
Introduce acid/base concepts, conjugate pairs, and Ka/pKa relationships.
10. Lewis Acids and CARDIO
Use CARDIO to evaluate acidity trends and assess electron delocalization.
11. Physical Properties
Relate structure and polarity to boiling point, solubility, and IMFs.
12. Acid/Base Review
Practice predicting acid/base strength and applying resonance to acidity.
13. Exam 1, in class
Students will be tested on bonding, resonance, and acid/base concepts.
14. Functional Groups and Isomerism
Identify common functional groups and distinguish constitutional isomers.
15. Naming Alkanes and Intermolecular Forces
Practice alkane nomenclature and analyze the impact of IMFs on physical properties.
16. Newman Projections
Learn to draw and interpret Newman projections and assess conformational energies.
17. Conformational Analysis
Explore energy profiles of staggered and eclipsed conformers.
18. Cycloalkanes and Strain
Understand ring strain and angle strain in cyclic structures.
19. Naming and Cis/Trans Isomers
Name substituted cycloalkanes and assign cis/trans stereochemistry.
20. Chair Conformations
Draw chair structures and identify axial vs. equatorial positions.
21. Chair Flips and Ring Fusion
Perform chair flips and analyze fused ring conformations and energies.
22. Cycloalkane Review
Reinforce 3D visualization, naming, and strain analysis of cyclic compounds.
23. Quiz 2, in class
Quiz on cycloalkanes and conformational analysis, followed by class review.
24. Chirality and Optical Activity
Identify chiral centers and understand how chirality relates to optical activity.
25. R/S Configuration
Assign R/S designations using the Cahn-Ingold-Prelog priority system.
26. Stereoisomers and Meso Compounds
Distinguish enantiomers, diastereomers, and meso compounds.
27. Isomer Classification and Prochirality
Classify molecules as chiral, achiral, or prochiral using structural features.
28. Stereochemistry Review
Review stereochemical concepts with in-depth structure analysis.
29. Reaction Types and Reactivity
Introduce reaction classes and the roles of nucleophiles and electrophiles.
30. Mechanism and Arrow-Pushing
Practice curved arrow notation and recognize reaction step patterns.
31. Thermodynamics and Energy Profiles
Discuss reaction energy diagrams, bond strength, and equilibrium.
32. Reaction Review
Work through mechanism and energy problems to reinforce concepts.
33. Exam 2, in class
Exam covering stereochemistry, reactions, mechanisms, and energetics.
34. Alkene Nomenclature and Structure
Name alkenes and calculate degrees of unsaturation.
35. Electrophilic Addition and Markovnikov
Understand general alkene addition mechanisms and regioselectivity.
36. Carbocation Rearrangement
Explore rearrangements like hydride and alkyl shifts in carbocation intermediates.
37. Halogenation and Oxymercuration
Learn addition reactions involving halogens and mercury(II) catalysts.
38. Hydroboration-Oxidation
Introduce anti-Markovnikov addition using BH₃ and hydrogen peroxide.
39. Epoxidation and Dihydroxylation
Predict stereochemical outcomes of syn and anti dihydroxylation reactions.
40. Alkene Reaction Review
Summarize and compare all major alkene addition mechanisms.
41. Quiz 3, in class
Quiz on alkene reactions and mechanisms, with review of each solution afterward.
42. Radical Additions and Peroxides
Learn how radicals change alkene addition outcomes via peroxide initiation.
43. Alkyne Nomenclature and Reactions
Name alkynes and describe hydration and halogenation pathways.
44. Reduction and Cleavage of Alkynes
Use Lindlar’s and Na/NH₃ to control stereoselective alkyne reduction.
45. Alkyne Review
Reinforce addition reactions, oxidations, and retrosynthetic pathways.
46. Alkyne Acidity and Alkylation
Use acetylide ions in nucleophilic substitution and carbon–carbon bond formation.
47. Radical Halogenation and Allylic Stability
Study allylic halogenation and the stability of allylic radicals.
48. Grignard Reagents
Learn how to form Grignard reagents and use them to build C–C bonds.
49. Organohalide Review
Review synthesis, mechanisms, and reactivity of halogenated organics.
50. Exam 3, in class
Students will be tested on alkene, alkyne, radical, and organometallic chemistry.
51. Substitution and Elimination Overview
Compare SN1, SN2, E1, and E2 pathways and identify determining factors.
52. SN2 Reactions and Stereochemistry
Understand backside attack, inversion of configuration, and rate dependencies.
53. SN1 and Carbocations
Learn the role of carbocations in SN1 and how rearrangements can occur.
54. E1 and E2 Mechanisms
Distinguish between E1 and E2 based on mechanism, conditions, and stereochemistry.
55. Competition and Prediction Practice
Predict which substitution or elimination mechanism dominates under given conditions.
56. Quiz 4, in class
Quiz on SN1, SN2, E1, and E2 with post-quiz review and discussion.
57. Multistep Synthesis
Practice combining reactions to achieve complex transformations.
58. IR Spectroscopy Introduction
Identify IR peaks for key functional groups based on bond vibrations.
59. IR Peak Assignments
Analyze IR spectra and match peaks to molecular structures.
60. Mass Spectrometry Basics
Learn fragmentation patterns, molecular ion peaks, and isotopic signatures.
61. Spectroscopy Practice Problems
Solve problems using IR and MS data to determine unknown structures.
62. Spectroscopy Review
Combine all spectroscopic tools to interpret and solve structural problems.
63. Exam 4, in class
Students will be tested on substitution/elimination and spectroscopy concepts.
64. Final Exam Review – Reactions and Mechanisms
Review key mechanisms from throughout the semester in preparation for the ACS exam.
65. Final Exam Review – Synthesis Strategy
Work through synthesis-based problems using multiple transformations.
66. Final Exam Review – Spectroscopy
Practice deducing structures using IR and MS data.
67. Final Exam Review – Isomers and Stereochemistry
Revisit all stereochemical concepts with a focus on chirality and R/S assignment.
68. Final Exam Review – Cumulative Practice
Complete a simulated ACS-style mini-exam and go over answers.
69. Final Exam Review – Student Q&A
Address any remaining questions and clarify difficult concepts.
70. Final Exam Preparation Wrap-Up
Close the semester with strategy tips and final reminders for exam success.
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