Course: Organic Chemistry 1

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Welcome to the Organic Chemistry 1 course, part of the Pre-Health Sciences Training Certificate series. This course is designed to provide learners interested in health-related programs and preparing for the MCAT with a comprehensive overview of fundamental principles in organic chemistry.
Throughout this course, you will cover topics such as organic compound nomenclature and functional groups, stereochemistry, structure and bonding, free radical reactions, substitution and elimination pathways, alkenes and alkynes, and alcohol structure, synthesis, and reactivity. Additionally, you will be introduced to synthetic strategies in organic chemistry. By the end of this course, you will have a strong foundation in the principles of organic chemistry that will help you to succeed in your future studies and careers.
The Organic Chemistry 1 course is sponsored in part by the International Development Research Centre and the University of the Incarnate Word School of Osteopathic Medicine. Like all NextGenU.org courses, it is competency-based, using competencies based on the Association of American Medical Colleges’ Medical College Admission Test. It uses learning resources from accredited, academic, professional, and world-class organizations and universities, such as Rice University. This course was designed by Alixandria Ali, BSc; Samantha Baboolal, BSc; Pablo Baldiviezo, MD, MSc, DiplEd; Sherian Bachan, MSc, BSc; Felix Emeka Anyiam, MPH, MScPH, DataSc; Marco Aurelio Hernandez, PhD, MSc, BSc; Kabiru Gulma, BPharm, PhD, MSc, MBA; Reisha Narine, MSc, BSc; and Aduke Williams, BA.
For publications on the efficacy of NextGenU.org’s courses, see NextGenU.org’s publication page.

There are nine (9) modules to complete, which provide an introduction to:
Module 1: Organic Compounds - Nomenclature and Functional Groups
Module 2: Stereochemistry
Module 3: Structure and Bonding
Module 4: Free Radical Reactions
Module 5: Mechanisms of Substitution and Elimination Pathways
Module 6: Alkenes
Module 7: Alkynes
Module 8: Alcohol - Structure, Synthesis, Reactivity
Module 9: Introduction to Synthetic Strategy
The completion time for this course is estimated at 49 hours, comprising 10 hours of learning resources, 20 hours of studying and assimilation of the content, and 19 hours of participating in learning activities and quizzes to assist learners in synthesizing learning materials. This course is equivalent to 1 credit hour in the U.S. undergraduate/ bachelor’s degree system.
The course requires the completion of all quizzes, discussion forums, and practical activities to receive a course certificate. Practice quizzes are available throughout the course and contain ten multiple-choice questions each. After completing each module, quiz, and learning activity, at the end of the course, you will have access to a final exam consisting of 40 multiple-choice questions and a chance to evaluate this course. Participants have up to three opportunities to take the final exam and achieve the required passing score of >=70%. Once you have passed the final exam and completed the evaluations, you can download a certificate of completion from NextGenU.org and our course’s co-sponsoring organizations.
We keep your personal information confidential, never sell any of your information, and only use anonymized data for research purposes. Also, we are happy to report your testing information and share your work with anyone (your school, employer, etc.) at your request.
Engaging with this Course:
This free course is for students who have graduated from high school and want to prepare to become a health professional and/or pass the MCAT exam. You may also browse this free course for your personal enrichment. There are no requirements.
To obtain a certificate, a learner must first register for the course and then successfully complete the following:
- The pre-test,
- All the reading requirements,
- All quizzes and pass with 70% with unlimited attempts,
- All case scenarios,
- All discussion forums,
- The final exam with a minimum of 70% and a maximum of 3 attempts, and
- The self and course evaluation forms.
To obtain credit:
- Complete all requirements listed above for the certificate, and
- Your learning institution or workplace should approve the partner-university-sponsored NextGenU.org course for educational credit, as they usually would for their learner taking a course anywhere.
NextGenU.org is happy to provide your institution with the following:
- A link to the description of the course training so they can see all of its components, including the co-sponsoring institution,
- Your grade on the final exam,
- Your work products (e.g., discussion forum responses) and any other required or optional shared materials you produce and authorize to share with them,
- Your evaluations -- course and self-assessments, and
- A copy of your certificate of completion with the co-sponsoring organizations listed.
To obtain a degree, NextGenU.org co-sponsors degree programs with institutional partners. To obtain a full degree co-sponsored with NextGenU.org, registrants must be enrolled in a degree program as a student of a NextGenU.org institutional partner. If you think your institution might be interested in offering a degree with NextGenU.org, contact us.
We hope you will find this a rewarding learning experience, and we count on your assessment and feedback to help us improve this training for future students.
Here are the next steps to take the course and earn a certificate:
- Complete the registration form,
- Take the pre-test, and
- Begin the course with Module 1: Organic Compounds - Nomenclature and Functional Groups. In each lesson, read the description, complete all required readings and any required activity, as well as take the corresponding quizzes.
Module 1: Organic Compounds - Nomenclature and Functional Groups
Instructional Goals covered in this module:
- Understand how to name compounds according to IUPAC rules and distinguish different functional groups and their properties.
Module 1: Lesson 1: Functional Groups and Families
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Understand the importance of functional groups and identify the fundamental properties they confer.
- Classify organic molecules by their functional groups.
Approximate time required for the readings for this lesson (at 144 words/minute): 45 minutes.

Click here to start this lesson
2 URLs
- Required Learning Resources and Activities
- Functional Groups Names, Properties, and Reactions URL
  Read the content under the headings "Functional Groups," "The Role of Functional Groups," and "Functional Groups and Reactivity." (5 minutes)
  UEN Digital Press with Pressbooks Open Educational Resources for Utah
- Functional Groups URL
  Read the entire page. (10 minutes)
  Lumenlearning - 2021
Module 1: Lesson 2: Alkanes
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Correctly name alkanes given their structure and molecular formula.
- Distinguish the most common reactions of alkanes.
- Describe conformational isomerisms of alkanes.
- Draw the different spatial representations of some simple alkanes by both sawhorse representation and Newman projection.
- Interpret energy versus bond rotation graphs for model alkanes, and interpret the relation to torsional strain.
Approximate time required for the readings for this lesson (at 144 words/minute): 2 hours and 24 minutes.

Click here to start this lesson
3 URLs
- Required Learning Resources and Activities
- Nomenclature URL
  Read the section on alkanes. (20 minutes)
  Virtual Textbook of Organic Chemistry Michigan State University - 2013
- Reactions of Alkanes URL
  Read the entire webpage. (13 minutes)
  Virtual Textbook of Organic Chemistry Michigan State University - 2013
- Alkane Conformational Analysis URL
  Read the entire webpage. (15 minutes)
  Kwantlen Polytechnic University - 2021
Module 1: Lesson 3: Cycloalkanes
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Correctly name cycloalkanes given their chemical formula or structural representation.
- Identify, name, and draw cis and trans stereoisomers of di-substituted cycloalkanes.
- Compare the energies of cycloalkanes, and explain ring strain.
- Visualize the conformations of cyclohexanes using models.
- Illustrate and identify axial versus equatorial substituents on cyclohexane chairs, and predict the most stable conformations of di-substituted cases.
Approximate time required for the readings for this lesson (at 144 words/minute): 3 hours and 26 minutes.

Click here to start this lesson
4 URLs, 1 Forum, 1 Quiz
- Required Learning Resources and Activities
- Cycloalkanes URL
  Read the content under the headings "The IUPAC Systematic Approach to Nomenclature" and "Cycloalkanes." (4 minutes)
  Virtual Textbook of Organic Chemistry Michigan State University
- Cycloalkanes and their Relative Stabilities URL
  Read the entire webpage. (6 minutes)
  Kwantlen Polytechnic University
- Conformation Analysis of Cyclohexane URL
  Read the entire webpage. (10 minutes)
- Substituted Cyclohexanes URL
  Read the entire webpage. (5 minutes)
- Learning Activity 1 - Organic Compounds - Nomenclature and Functional Groups (2 hours) Forum
  General Instructions
  In this activity, you will be given a series of questions. These questions will involve naming alkenes from their molecular structure, drawing structures from given names, examining energy diagrams of different conformations, and investigating stability based on conformation. The link to a chemistry drawing tool is provided; you should explore the features and familiarize yourself with the functions before starting the activity. Note that you are not required to share the structures or mechanisms you drew when sharing your responses.
  Step 1 - Review
  Review the material from this module, paying particular attention to the different representations used for alkanes and factors affecting stability.
  Step 2 - Respond
  Answer the following questions:
  Explain the process of naming alkanes using the IUPAC rules for the structures below:
  
  Using the chemistry tool, draw the structures for the alkanes below and explain the process you used in determining the structure:
  2, 3 dimethyl-heptane
  3-ethyl-2-methyl-heptane
  1, 2-dimethylcyclohexane
  
  Examine the information presented and discuss the points below:
  
  What does this graph aim to represent?
  Why is the eclipsed formation more stable?
  Why is there rapid rotation at room temperature?
  
  Cis/Trans nomenclature can be used to describe the relative positioning of substituents on molecules with more complex ring structures. Examine the molecular structure provided below:
  Are the OH and the adjacent methyl group cis or trans to each other?
  What can you deduce about the relative positions of the indicated hydrogens?
  
  Which of these chair conformations are the most stable and why?
  
  Step 3: Share
  You are required to share your answers to Questions 1, 3, 4, and 5.
  To share your work, click the “Add a new discussion topic” button under this post and paste your work into the “Message” box. Make sure to reference others’ intellectual property when necessary. All references should follow 7th Edition APA formatting. For further instructions, see the resource on the Himmelfarb Health Sciences Library: APA citation resource (N.B.: references are excluded from word counts).
  Step 4: Interact
  To complete the activity, evaluate and categorize the work from one of your peers based on items A - E of the rubric below. Provide a rationale for your grade and comments or suggestions for improvement. To post a reply, click “Reply” on a particular discussion, write your feedback, and click “Post to forum.” You can use the list below as an example:
  Item A is .…. because…. My suggestions for improvement are….
  Item B is .…. because…. My suggestions for improvement are…
  Item C is .…. because…. My suggestions for improvement are….
  Item D is .…. because…. My suggestions for improvement are….
  Item E is .…. because…. My suggestions for improvement are….
- Quiz: Module 1
Module 2: Stereochemistry
Instructional Goals covered in this module:
- Understand the spatial arrangement, properties, and reactivity of stereoisomers.
- This module will act as foundation for the rest of the course, providing you with an understanding of the physiology of the breast.
Module 2: Lesson 1: Geometric Isomers and the E/Z Naming System
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Name the geometric isomers of alkenes using the E/Z naming system.
Approximate time required for the readings for this lesson (at 144 words/minute): 21 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Geometric Isomers and E/Z Naming System URL
  Read the entire webpage. (7 minutes)
  Kwantlen Polytechnic University
Module 2: Lesson 2: Enantiomers
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Explain the difference between achiral and chiral molecules with mirror planes of symmetry and carbon hybridization.
- Contrast between R and S configuration using Cahn-Ingold-Prelog System.
- Assign the priority of the substituents attached to the chiral center.
Approximate time required for the readings for this lesson (at 144 words/minute): 33 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Chirality and R/S Naming System URL
  Read the entire webpage. (11 minutes)
  Kwantlen Polytechnic University - 2021
Module 2: Lesson 3: Optical Activity
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Identify when a compound is optically active.
- Explain the significance of optical activity in racemic mixtures.
- Describe the role of chirality in nature.
Approximate time required for the readings for this lesson (at 144 words/minute): 45 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Optical Activity URL
  Read the entire webpage. (15 minutes)
  Kwantlen Polytechnic University
Module 2: Lesson 4: Fisher Projection
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Convert between stereo structures and Fischer projections.
Approximate time required for the readings for this lesson (at 144 words/minute): 9 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Fisher Projection URL
  Read the entire webpage. (3 minutes)
  Kwantlen Polytechnic University
Module 2: Lesson 5: Compounds with More Than One Chirality Centers
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Identify stereogenic centers in organic molecules.
- Distinguish between different types of isomers, including enantiomers and diastereomers.
- Appraise the maximum number of isomers possible in a compound with more than one stereogenic center.
Approximate time required for the readings for this lesson (at 144 words/minute): 2 hours and 41 minutes.

Click here to start this lesson
1 URL, 1 Forum, 1 Quiz
- Required Learning Resources and Activities
- Compounds with More Than One Chirality Centers URL
  Read the entire webpage. (10 minutes)
  Kwantlen Polytechnic University
- Learning Activity 2 - Stereochemistry (2 hours) Forum
  General Instructions
  In this activity, you will be given a series of questions. These questions will involve identifying molecular relationships, explaining Fischer projections, and identifying isomers from a given structure. The link to a chemistry drawing tool is provided; you should explore the features and familiarize yourself with the functions before starting the activity. Note that you are not required to share the structures or mechanisms you drew when sharing your responses.
  Step 1 - Review
  Review the material from this module, paying particular attention to chirality, stereogenicity, and Fischer projections.
  Step 2 - Respond
  Answer the following questions:
  Determine the relationship for each pair of molecules (enantiomers, identical, constitutional isomers, non-isomer) and provide brief explanations of the reasoning behind your answers.
  
  When drawing Fischer Projections, if the lowest priority group is on a horizontal bond (as in the following structure), we determine the priority decrease direction, then reverse the answer to the opposite way to get the final configuration. In your own words, explain why this procedure is followed.
  Use the chemistry tool to draw the structures of all the stereoisomers for 1-bromo-2-chlorocyclobutane. Then, describe your approach and indicate the relationship between the stereoisomers.
  Step 3: Share
  To share your work, click the “Add a new discussion topic” button under this post and paste your work into the “Message” box. Make sure to reference others’ intellectual property when necessary. All references should follow 7th Edition APA formatting. For further instructions, see the resource on the Himmelfarb Health Sciences Library: APA citation resource (N.B.: references are excluded from word counts). You do not need to share your drawings in the Chemistry tool, but you can discuss them if required.
  Step 4: Interact
  To complete the activity, evaluate and categorize the work from one of your peers based on items A - E of the rubric below. Provide a rationale for your grade and comments or suggestions for improvement. To post a reply, click “Reply” on a particular discussion, write your feedback and click “Post to forum.” You can use the list below as an example:
  Item A is .…. because…. My suggestions for improvement are….
  Item B is .…. because…. My suggestions for improvement are….
  Item C is .…. because…. My suggestions for improvement are….
  Item D is .…. because…. My suggestions for improvement are….
  Item E is .…. because…. My suggestions for improvement are….
- Quiz: Module 2
  To access the quiz, click on the name of the quiz provided above. On the following screen, click the attempt quiz button to view the case studies and respond to the questions.
Module 3: Structure and Bonding
Instructional Goals covered in this module:
- Understand the relationship between the structure, bonding, reactivity, and stability of organic molecules.
- After reading the resources and participating in the activities in this module, you will become familiar with the presentation of benign breast disorders, their work-up, treatment, and management.
Module 3: Lesson 1: Review of Structure and Bonding
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Describe the four quantum numbers and identify the ranges of possible values for each number.
- Describe the stability and energy of bonding and antibonding orbitals.
- Describe the electron configuration directly from the quantum numbers and Hund's rule.
- Explain how adding a double or triple bond affects a molecule's electron density and molecular orbitals.
- Describe the significance of electron density in conjugation and resonance.
- Identify the hybridization of an atom within a complex molecule.
Approximate time required for the readings for this lesson (at 144 words/minute): 3 hours and 39 minutes.

Click here to start this lesson
4 URLs
- Required Learning Resources and Activities
- Quantum Numbers for Atoms URL
  Read the entire webpage. (15 minutes)
  LibreTexts Chemistry - 2022
- Molecular Orbital Theory URL
  Read the entire webpage. (30 minutes)
  Pressbooks - Rice University - 2022
- Double and Triple Bonds URL
  Read the entire webpage. (5 minutes)
  LibreTexts Chemistry - 2022
- Resonance URL
  Read the entire webpage. (23 minutes)
  LibreTexts Chemistry - 2020
Module 3: Lesson 2: Chemical Bonding Theory
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Use the common methods of drawing structures that originate from the Lewis structures (General Chemistry): expanded formula, condensed formula, and skeletal structures.
- Use the octet rule and bonds/lone pairs.
Approximate time required for the readings for this lesson (at 144 words/minute): 45 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Bonding & Molecular Structure URL
  Read the entire webpage. (15 minutes)
  Michigan State University - 2013
Module 3: Lesson 3: Chemical Bonds
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Draw organic structures using formal charges.
- Distinguish single, double, and triple bonds in hydrocarbons and high-energy intermediate species (i.e., carbocation, carbanion, carbon radical).
- Identify the formation of ionic and covalent bonds.
Approximate time required for the readings for this lesson (at 144 words/minute): 1 hour and 3 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Drawing Organic Structures URL
  Read the entire webpage. (21 minutes)
Module 3: Lesson 4: Resonance
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Distinguish the contribution of electron pairs to the repulsive forces that govern the geometry of individual molecules.
- Appraise the contributions of resonance to hybrids and energy.
- Apply the concept of formal charges to distinguish suitable resonance structures.
Approximate time required for the readings for this lesson (at 144 words/minute): 1 hour.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Resonance URL
  Read the entire webpage. (20 minutes)
  Chemistry Libre texts - 2020
Module 3: Lesson 5: Review of Molecular Orbital Theory
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Describe the stability and energy of bonding and antibonding orbitals.
- Explain how adding a double or triple bond affects a molecule's electron density and molecular orbitals.
- Order the different orbital types based on strength.
- Describe the relationship between conjugation and thermodynamic stability.
- Contrast conjugated pi bonds and isolated pi bonds.
Approximate time required for the readings for this lesson (at 144 words/minute): 3 hours and 18 minutes.

Click here to start this lesson
2 URLs
- Required Learning Resources and Activities
- Molecular Orbital Theory URL
  Read the entire webpage. (48 minutes)
  Chemistry Libre Text - 2022
- Molecular Orbital Theory- Conjugation and Aromaticity URL
  Read the entire webpage. (18 minutes)
Module 3: Lesson 6: Hybridization
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Evaluate the percentage of s character present in a given hybridization level, such as sp2.
- Describe the relationship between electron density and resonance structures.
- Identify the hybridization of an atom within a complex molecule.
- Identify sp3 hybridized carbons in a conjugated system.
Approximate time required for the readings for this lesson (at 144 words/minute): 27 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Hybridization URL
  Read the content under the heading "Hybridization." (9 minutes)
  Chemistry libre texts - 2022
Module 3: Lesson 7: Acidity of Organic Molecules
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Identify common functional groups that act as acids or bases.
- Describe how electrons move in reactions by learning about electron-donating and electron-withdrawing groups.
Approximate time required for the readings for this lesson (at 144 words/minute): 36 minutes.

Click here to start this lesson
2 URLs
- Required Learning Resources and Activities
- Lewis Acids and Lewis Bases URL
  Read the entire webpage. (5 minutes)
  Kwantlen Polytechnic University
- All Other Things Being Equal Electron Withdrawing Groups Tend to Make Lewis Acids Stronger and Bases Weaker While Electron Donating Groups Tend to Make Lewis Bases Stronger and Acids Weaker URL
  Read the entire webpage. (7 minutes)
  Chemistry Libre texts - 2022
Module 3: Lesson 8: Bond Length and Strength
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Determine bond order, bond length, and bond strength from Lewis structures.
- Apply the periodic table trends to relate bond strength to bond order.
Approximate time required for the readings for this lesson (at 144 words/minute): 2 hours and 23 minutes.

Click here to start this lesson
1 URL, 1 Forum, 1 Quiz
- Required Learning Resources and Activities
- Bond Lengths, Bond Strengths, and Bond Angles URL
  Read the content under the heading "Bond Length." (4 minutes)
  Chemistry Libre texts - 2014
- Learning Activity 3 - Structure and Bonding (2 hours) Forum
  General Instructions
  In this activity, you will be given a series of questions. These questions will involve identifying the placement of formal charges, discussing resonance, and discussing hybridization. The link to a chemistry drawing tool is provided; you should explore the features and familiarize yourself with the functions before starting the activity. Note that you are not required to share the structures or mechanisms you drew when sharing your responses.
  Step 1 - Review
  Review the material from this module, paying particular attention to formal charges, resonance structures, hybridization, and electron mechanisms.
  Step 2 - Respond
  Answer the following questions:
  Examine the molecular structure below. The structure should have a net charge of -2. Where would you place the formal charges? Explain your reasoning.
  Benzene is a common organic solvent previously used in gasoline; it is no longer used for this purpose, however, because it is now known to be a carcinogen. The benzene molecule (C6H6) consists of a regular hexagon of carbon atoms, each of which is also bonded to a hydrogen atom. Use the concept of resonance to describe the bonding in benzene. You can use the chemistry tool to draw and visualize the resonance structures to help you.
  
  Based on resonance conformation, which structure is more stable?
  
  Determine the hybridization (sp, sp2, sp3) of the indicated atom and indicate the atom's shape from the Lewis structures below:
  The Carbon
  
  The Oxygen
  Step 3: Share
  To share your work, click the “Add a new discussion topic” button under this post and paste your work into the “Message” box. Make sure to reference others’ intellectual property when necessary. All references should follow 7th Edition APA formatting. For further instructions, see the resource on the Himmelfarb Health Sciences Library: APA citation resource (N.B.: references are excluded from word counts). Note that you do not need to share your drawings done in the Chemistry tool, but you can discuss them if needed.
  Step 4: Interact
  To complete the activity, evaluate and categorize the work from one of your peers based on items A - E of the rubric below. Provide a rationale for your grade and comments or suggestions for improvement. To post a reply, click “Reply” on a particular discussion, write your feedback, then click “Post to forum.” You can use the list below as an example:
  Item A is .…. because…. My suggestions for improvement are….
  Item B is .…. because…. My suggestions for improvement are….
  Item C is .…. because…. My suggestions for improvement are….
  Item D is .…. because…. My suggestions for improvement are….
  Item E is .…. because…. My suggestions for improvement are….
- Quiz: Module 3
  To access the quiz, click on the name of the quiz provided above. On the following screen, click the attempt quiz button to view the case studies and respond to the questions.
Module 4: Free Radical Reactions
Instructional Goals covered in this module:
- Understand the reactivity of the free radical reactions of alkanes.
- This module will provide an overview of the screening and management of selected diseases of the breast such as Mastitis, Galactorrhea, Mastodynia, and Breast Masses.
Module 4: Lesson 1: Free Radicals
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Investigate the conditions and methods used to form free radicals.
- Describe the geometry of radicals and relative radical stabilities.
Approximate time required for the readings for this lesson (at 144 words/minute): 45 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Organic Radicals URL
  Read the content under the heading "Organic Radicals." (15 minutes)
  Michigan State University Online textbook - 2013
Module 4: Lesson 2: Free Radical Substitution Reaction of Alkanes
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Distinguish the difference between homolytic and heterolytic cleavage.
- Describe the three phases (initiation, propagation, and termination) of radical chain reaction with radical initiators involved in homolytic cleavage.
- Apply homolytic bond dissociation energies to describe the energy level diagram and the propagation process.
- Compare the energy changes for halogenation (substitution) between halogens.
Approximate time required for the readings for this lesson (at 144 words/minute): 45 minutes.

Click here to start this lesson
2 URLs
- Required Learning Resources and Activities
- Homolytic and Heterolytic Cleavage URL
  Read sections 1-4 under "Organic Chemicals." (5 minutes)
  Kwantlen Polytechnic University
- Halogenation Reaction of Alkanes URL
  Read the entire section. (10 minutes)
  Kwantlen Polytechnic University
Module 4: Lesson 3: Stability of Alkyl Radicals
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Determine the stability trends of proposed radical intermediates.
- Link radical chain processes to the regioselectivity of alkyl radicals.
- Appraise the mechanisms of resonance stabilized benzylic and allylic radicals.
Approximate time required for the readings for this lesson (at 144 words/minute): 9 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Stability of Alkyl Radicals URL
  Read the entire section. (3 minutes)
  Kwantlen Polytechnic University - 2021
Module 4: Lesson 4: Stereochemistry for Halogenation of Alkanes
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Compare the relative reaction rate of alkyl radicals for chlorination and bromination.
- Breakdown the propagation steps of halogenation of alkanes to appraise stereochemistry in the radical substitution reactions.
Approximate time required for the readings for this lesson (at 144 words/minute): 2 hours and 32 minutes.

Click here to start this lesson
2 URLs, 1 Forum, 1 Quiz
- Required Learning Resources and Activities
- Chlorination vs. Bromination URL
  Read the entire section. (5 minutes)
  Kwantlen Polytechnic University - 2021
- Stereochemistry for Halogenation of Alkanes URL
  Read the entire section. (2 minutes)
  Kwantlen Polytechnic University - 2021
- Learning Activity 4 - Free Radical Reactions (2 hours) Forum
  General Instructions
  In this activity, you will be given a series of questions. These questions will involve calculating reaction energy, explaining radical stability, and discussing mechanisms of propagation. The link to a chemistry drawing tool is provided; you should explore the features and familiarize yourself with the functions before starting the activity. Note that you are not required to share the structures or mechanisms you drew when sharing your responses.
  Step 1 - Review
  Review the material from this module, paying particular attention to propagation, resonance, radicals, and halogenation.
  Step 2 - Respond
  Answer the following questions:
  Refer to the bond energies in the table below and calculate the reaction energy for the propagation step of the mono-chlorination of methane. Explain your method.
  
  The resonance effect is responsible for the stability of the benzylic radical. Explain resonance as it applies to the benzylic radical. Be sure to include the movement of the electron.
  You can use the chemistry tool to draw out the resonance mechanism to help you explain.
  
  The experiment results of the bromination reaction of (±)-3-methylhexane indicate that the racemic mixture of R and S 3-bromo-3-methylhexane were obtained with the bromination. Explain the stereochemistry of the propagation steps in the mechanism for this reaction. You can use the Chemistry tool to draw out the resonance mechanism to help you explain.
  Step 3: Share
  To share your work, click the “Add a new discussion topic” button under this post and paste your work into the “Message” box. Make sure to reference others’ intellectual property when necessary. All references should follow 7th Edition APA formatting. For further instructions, see the resource on the Himmelfarb Health Sciences Library: APA citation resource (N.B.: references are excluded from word counts). Note that you do not need to share your drawings done in the Chemistry tool, but you can discuss them if needed.
  Step 4: Interact
  To complete the activity, evaluate and categorize the work from one of your peers based on items A - E of the rubric below. Provide a rationale for your grade and comments or suggestions for improvement. To post a reply, click “Reply” on a particular discussion, write your feedback, then click “Post to forum.” You can use the list below as an example:
  Item A is .…. because…. My suggestions for improvement are….
  Item B is .…. because…. My suggestions for improvement are….
  Item C is .…. because…. My suggestions for improvement are….
  Item D is .…. because…. My suggestions for improvement are….
  Item E is .…. because…. My suggestions for improvement are….
- Quiz: Module 4
  To access the quiz, click on the name of the quiz provided above. On the following screen, click the attempt quiz button to respond to the questions.
Module 5: Mechanisms of Substitution and Elimination Pathways
Instructional Goals covered in this module:
- Understand the mechanisms of substitution and elimination reactions.
- This module will provide you with an overview of the epidemiology of breast cancer as well as the evaluation and effective counseling of patients with a risk for breast cancer.
Module 5: Lesson 1: Nucleophilic Substitution Reaction Overview
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Distinguish nucleophiles, electrophiles, and leaving groups in substitution reactions.
- Appraise the relationship between the electrophile and the leaving group in a substitution reaction.
- Explain the difference between electron-rich and electron-poor atoms.
Approximate time required for the readings for this lesson (at 144 words/minute): 18 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Nucleophilic Substitution Reaction Overview URL
  Read the entire section. (6 minutes)
  Kwantlen Polytechnic University
Module 5: Lesson 2: SN2 Reaction Mechanism, Energy Diagram, and Stereochemistry
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Explain the SN2 mechanism by identifying the electron pair transfers, nucleophile attack, and leaving group.
- Breakdown potential energy diagrams of substitution SN2 reactions to determine main reaction steps, activation energy, transition states, and reaction intermediates.
- Deduce the effect of alkyl halide structure on SN2 reaction rate.
- Compare the R/S configuration of the groups of products and reactants to appraise stereochemistry.
- Compare the relative reactivity of nucleophiles and leaving groups in SN2 reactions.
Approximate time required for the readings for this lesson (at 144 words/minute): 1 hour.

Click here to start this lesson
2 URLs
- Required Learning Resources and Activities
- SN2 Reaction Mechanism, Energy Diagram, and Stereochemistry URL
  Read the content under the headings "SN2 Reaction Mechanism," "Energy Diagram," and "Stereochemistry." (10 minutes)
  Kwantlen Polytechnic University - 2021
- Other Factors that Affect SN2 Reactions URL
  Read the entire section. (10 minutes)
  Kwantlen Polytechnic University - 2021
Module 5: Lesson 3: SN1 Reaction Mechanism, Energy Diagram, and Stereochemistry
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Explain the reaction steps and stereochemistry of the SN1 reaction mechanism.
- Appraise the effect of substrate structure on SN1 reaction rate.
- Examine the relative stability of carbocations.
Approximate time required for the readings for this lesson (at 144 words/minute): 45 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- SN1 Reaction Mechanism, Energy Diagram, and Stereochemistry URL
  Read the content under the heading "SN1 Reaction Mechanism." (15 minutes)
  Kwantlen Polytechnic University - 2021
Module 5: Lesson 4: SN1 vs. SN2
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Distinguish the solvent effects on SN1 and SN2 reactions.
Approximate time required for the readings for this lesson (at 144 words/minute): 30 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- SN1 vs. SN2 URL
  Read the entire section. (10 minutes)
  Kwantlen Polytechnic University
Module 5: Lesson 5: Extra Topics on Nucleophilic Substitution Reaction
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Explain the SN1 reaction mechanisms with carbocation rearrangement.
- Explain the mechanism that rationalizes the structure and stereochemistry of intramolecular nucleophilic substitution reactions and how to convert a poor leaving group to a good leaving group.
Approximate time required for the readings for this lesson (at 144 words/minute): 27 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Extra Topics on Nucleophilic Substitution Reaction URL
  Read the entire section. (9 minutes)
  Kwantlen Polytechnic University
Module 5: Lesson 6: Elimination Reactions
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Describe the general mechanism of the elimination reaction and identify the alpha and beta carbon, taking the leaving group as a reference.
- Explain the E2 reaction mechanism.
- Examine the regioselectivity of the E2 reaction using Zaitsev’s rule and the Hofmann rule.
- Examine the stereochemistry of E2 reaction.
- Explain the two steps involved in the E1 reaction mechanism.
Approximate time required for the readings for this lesson (at 144 words/minute): 1 hour and 36 minutes.

Click here to start this lesson
3 URLs
- Required Learning Resources and Activities
- Elimination Reactions URL
  Read the entire section. (5 minutes)
  Kwantlen Polytechnic University
- E2 Reactions URL
  Read the entire section. (20 minutes)
  Kwantlen Polytechnic University - 2021
- E1 Reactions URL
  Read the entire section. (7 minutes)
  Kwantlen Polytechnic University
Module 5: Lesson 7: Reaction Rates of Substitution and Elimination Reactions
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Distinguish whether compounds are most likely to go through elimination or substitution reactions.
- Compare the reaction rates of substitution and elimination reactions.
- Predict the distribution between E2-elimination and SN2 substitution for reactions of haloalkanes.
Approximate time required for the readings for this lesson (at 144 words/minute): 2 hours and 40 minutes.

Click here to start this lesson
1 URL, 1 Forum, 1 Quiz
- Required Learning Resources and Activities
- Comparison and Competition Between SN1, SN2, E1, and E2 URL
  Read the entire section. (10 minutes)
  Kwantlen Polytechnic University
- Learning Activity 5 - Mechanisms of Substitution and Elimination Pathways (2 hours) Forum
  General Instructions
  In this activity, you will be given a series of questions. These questions will involve discussing SN1 and SN2 mechanisms, interpreting energy profile diagrams, discussing E1 and E2 mechanisms, and distinguishing between Hofmann and Zaitsev’s rule. The link to a chemistry drawing tool is provided; you should explore the features and familiarize yourself with the functions before starting the activity. Note that you are not required to share the structures or mechanisms you drew when sharing your responses.
  Step 1 - Review
  Review the material from this module, paying particular attention to SN1, SN2, E1, and E2 reaction mechanisms.
  Step 2 - Respond
  Answer the following questions:
  What does the energy profile diagram below tell us about the reaction between CH3Br and OH- ?
  
  Use the following questions to prompt your discussion:
  Is this SN1 or SN2?
  What does it tell us about the energy of the products and reactants?
  What does T.S. represent? What is its significance?
  Explain the steps of the reaction mechanism that would be involved. You can practice drawing the mechanism in the chemistry tool.
  
  What does the energy profile diagram below tell us about the reaction between (CH3)3CBr and H2O?
  
  Use the following questions to prompt your discussion:
  Is this SN1 or SN2?
  What does it tell us about the energy of the products and reactants?
  What is “intermediate”? What is its significance?
  Explain the steps of the reaction mechanism that would be involved. You can practice drawing the mechanism in the chemistry tool.
  
  Name and describe the mechanism for the reaction below. You can practice drawing the mechanism in the chemistry tool.
  
  Examine the two reactions presented below and answer the questions that follow.
  
  Distinguish which equation follows the Hofmann rule and which follows Zaitsev’s rule with a brief explanation of your reasoning.
  What are the conditions needed for each reaction to follow its respective rule?
  For the equation that follows the Hofmann rule, describe the mechanism. You can practice drawing the mechanism in the chemistry tool.
  
  Step 3: Share
  To share your work, click the “Add a new discussion topic” button under this post and paste your work into the “Message” box. Make sure to reference others’ intellectual property when necessary. All references should follow 7th Edition APA formatting. For further instructions, see the resource on the Himmelfarb Health Sciences Library: APA citation resource (N.B.: references are excluded from word counts). Note that you do not need to share your drawings done in the Chemistry tool, but you can discuss them if needed.
  Step 4: Interact
  To complete the activity, evaluate and categorize the work from one of your peers based on items A - E of the rubric below. Provide a rationale for your grade and comments or suggestions for improvement. To post a reply, click “Reply” on a particular discussion, write your feedback, then click “Post to forum.” You can use the list below as an example:
  Item A is .…. because…. My suggestions for improvement are….
  Item B is .…. because…. My suggestions for improvement are….
  Item C is .…. because…. My suggestions for improvement are….
  Item D is .…. because…. My suggestions for improvement are….
  Item E is .…. because…. My suggestions for improvement are….
- Quiz: Module 5
  To access the quiz, click on the name of the quiz provided above. On the following screen, click the attempt quiz button to respond to the questions.
Module 6: Alkenes
Instructional Goals covered in this module:
- Understand the reactivity and stereochemistry of alkenes.
- In this module, you will learn about common inheritance patterns of breast cancer and indications for screening for certain genes related to breast cancer.
Module 6: Lesson 1: Nomenclature, Structure, and Synthesis of Alkenes
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Use the IUPAC rules to name and draw the structure of alkenes.
Approximate time required for the readings for this lesson (at 144 words/minute): 15 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Organic Nomenclature URL
  Read the section on alkenes. (5 minutes)
  Virtual Textbook of Organic Chemistry Michigan State University - 2013
Module 6: Lesson 2: Synthesis of Alkenes
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Explain the mechanisms and distinguish the major products when alkenes are synthesized through acid-catalyzed dehydration of alcohols and dehydrohalogenation of alkyl halides.
Approximate time required for the readings for this lesson (at 144 words/minute): 45 minutes.

Click here to start this lesson
1 URL
- Required Learning Resources and Activities
- Synthesis of Alkenes URL
  Read the entire section. (15 minutes)
  Kwantlen Polytechnic University
Module 6: Lesson 3: Reactivity of Alkenes
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Explain the main two steps involved in the mechanism of the addition reaction.
- Deduce the main products formed from electrophilic additions through regioselectivity (Markovnikov’s rule).
- Explain the mechanism and products formed through the radical addition of HBr and compare it to electrophilic addition.
- Explain the mechanism for acid-catalyzed hydration of alkenes with water and alcohols.
- Break down the mechanism and stereochemistry of electrophilic additions of halogens.
- Appraise the mechanism for the catalytic hydrogenation reaction.
- Apply the principles of electrophilic addition to explain the mechanism of oxymercurations of alkenes.
- Question the hydroboration-oxidation reaction mechanism of alkenes.
- Explain the electronic and steric effects which determine the stereochemistry of hydroboration.
- Break down the steps of the oxidation and hydrolysis of trialkylboranes.
- Appraise the reaction mechanisms of common oxidation reactions of alkenes.
Approximate time required for the readings for this lesson (at 144 words/minute): 5 hours and 25 minutes.

Click here to start this lesson
6 URLs, 1 Forum, 1 Quiz
- Required Learning Resources and Activities
- Addition of Hydrogen Halide to Alkenes URL
  Read the entire section. (10 minutes)
  Kwantlen Polytechnic University - 2021
- Addition of Water (or Alcohol) to Alkenes URL
  Read the entire section. (5 minutes)
  Kwantlen Polytechnic University - 2021
- Addition of Bromine and Chlorine to Alkenes URL
  Read the entire section. (15 minutes)
  Kwantlen Polytechnic University - 2021
- Hydrogenation URL
  Read the entire section. (5 minutes)
  Kwantlen Polytechnic University - 2021
- Two Other Hydration Reactions of Alkenes URL
  Read the entire section. (15 minutes)
  Kwantlen Polytechnic University - 2021
- Oxidation Reactions of Alkenes URL
  Read the entire section. (15 minutes)
  Kwantlen Polytechnic University - 2021
- Learning Activity 6 - Alkenes (2 hours) Forum
  General Instructions
  In this activity, you will be given a series of questions. These questions will involve explaining reaction mechanisms that involve alcohols, explaining the stereochemistry of reactions, and discussing Markovnikov’s rule. The link to a chemistry drawing tool is provided; you should explore the features and familiarize yourself with the functions before starting the activity. Note that you are not required to share the structures or mechanisms you drew when sharing your responses.
  Step 1 - Review
  Review the material from this module, paying particular attention to the different mechanisms of alkene reactions, Markovnikov’s rule, and stereochemistry.
  Step 2 - Respond
  Answer the following questions:
  Examine the reaction below and answer the questions
  What is the name of this reaction?
  What type of mechanism does this reaction follow? (SN1, SN2, E1, E2)
  What are the names of the reactants and products?
  Explain each step of the mechanism of this reaction.
  
  Explain the mechanism of this reaction:
  
  You can practice drawing the mechanism in the chemistry tool.
  Below are the first two steps of a reaction mechanism:
  What reaction is this?
  Explain what happens between the 2o and 3o carbocations. Why is this necessary?
  Complete the reaction by describing what happens in step 3 of the mechanism and include an explanation on the stability of the end product or products. You can practice drawing the mechanism in the chemistry tool.
  The mechanism of the addition reaction on an alkene involves two steps. Look at the reaction below and answer the questions that follow.
  Is the product shown the only product of this reaction?
  If there are multiple products, which is the major product and why? If there is only one product, explain why.
  Are carbocations formed in this reaction?
  Describe the mechanism of this reaction. You can practice drawing the mechanism in the chemistry tool.
  Examine the reaction below. The second step of the mechanism is also provided. Explain the entire mechanism and be sure to mention the rules that may apply. You can practice drawing the mechanism in the chemistry tool.
  
  Examine the reaction below.
  
  Explain the mechanism with reference to anti-Markovnikov regioselectivity.
  Step 3: Share
  To share your work, click the “Add a new discussion topic” button under this post and paste your work into the “Message” box. Make sure to reference others’ intellectual property when necessary. All references should follow 7th Edition APA formatting. For further instructions, see the resource on the Himmelfarb Health Sciences Library: APA citation resource (N.B.: references are excluded from word counts). Note that you do not need to share your drawings done in the Chemistry tool, but you can discuss them if needed.
  Step 4: Interact
  To complete the activity, evaluate and categorize the work from one of your peers based on items A - E of the rubric below. Provide a rationale for your grade and comments or suggestions for improvement. To post a reply, click “Reply” on a particular discussion, write your feedback, then click “Post to forum.” You can use the list below as an example:
  Item A is .…. because…. My suggestions for improvement are….
  Item B is .…. because…. My suggestions for improvement are….
  Item C is .…. because…. My suggestions for improvement are….
  Item D is .…. because…. My suggestions for improvement are….
  Item E is .…. because…. My suggestions for improvement are….
- Quiz: Module 6
  To access the quiz, click on the name of the quiz provided above. On the following screen, click the attempt quiz button to respond to the questions.
Module 7: Alkynes
Instructional Goals covered in this module:
- Understand the nomenclature, synthesis, and reaction mechanisms of alkynes.
Module 7: Lesson 1: Nomenclature, Reactivity, and Synthesis of Alkynes
Student Learning Outcomes:
Upon completion of this lesson, you will be able to:
- Apply the IUPAC rules to name and draw the structure of alkynes.
- Compare the acidity of terminal alkynes to alkanes and alkenes and explain the mechanism for the deprotonation of a terminal alkyne by strong bases.
- Explain the reaction mechanism for the synthesis of internal and terminal alkynes by dehydrohalogenation.
- Break down the catalytic hydrogenation reactions of alkynes and explain the hydrogenation (reduction) by a metal.
- Apply knowledge of Markovnikov’s regioselectivity to examine the hydrohalogenation of alkynes.
- Break down the products formed from the acid-catalyzed addition of water to alkynes.
- Explain the two steps involved in the hydroboration-oxidation of alkynes and deduce the products formed.
Approximate time required for the readings for this lesson (at 144 words/minute): 2 hours and 54 minutes.

Click here to start this lesson
2 URLs, 1 Forum, 1 Quiz
- Required Learning Resources and Activities
- Organic Nomenclature URL
  Read the section on alkynes. (5 minutes)
  Virtual Textbook of Organic Chemistry Michigan State University - 2013
- Alkyne Reactivity URL
  Read the entire section. (11 minutes)
  Kwantlen Polytechnic University - 2021
- Learning Activity 7 - Alkynes (2 hours) Forum
  General Instructions
  In this activity, you will be given a series of questions. These questions will involve explaining mechanisms for alkyne reactions and discussing regioselectivity and tautomerism. The link to a chemistry drawing tool is provided; you should explore the features and familiarize yourself with the functions before starting the activity. Note that you are not required to share the structures or mechanisms you drew when sharing your responses.
  Step 1 - Review
  Review the material from this module, paying particular attention to the different mechanisms of alkyne reactions, Markovnikov’s rule, and the use of catalysts.
  Step 2 - Respond
  
  Answer the following questions:
  Alkynes can be synthesized by the following scheme:
  
  With reference to the scheme, design the synthesis route of 1-pentyne from 1-pentene and explain its mechanism. You can practice drawing the mechanism in the chemistry tool.
  Explain the use of platinum or palladium catalysts in hydrogenation reactions of alkynes. Are there any special conditions required when using these catalysts?
  Internal alkyne can be converted into trans-alkene using sodium (or lithium) in liquid ammonia. Explain the mechanism of this type of reaction. The general scheme is provided below. You can practice drawing the mechanism in the chemistry tool.
  
  Look at the reaction below and answer the questions that follow
  What is the name of this reaction?
  Explain the mechanism of the reaction. You can practice drawing the mechanism in the chemistry tool.
  Explain the regioselectivity that occurs to give the final product.
  Hydroboration oxidation reactions result in tautomerization. Examine the incomplete reaction scheme below.
  Complete the reaction mechanism for both pathways and explain what happens. You can practice drawing the mechanism in the chemistry tool.
  Explain the concept of tautomerism and why it occurs here.
  Step 3: Share
  
  To share your work, click the “Add a new discussion topic” button under this post and paste your work into the “Message” box. Make sure to reference others’ intellectual property when necessary. All references should follow 7th Edition APA formatting. For further instructions, see the resource on the Himmelfarb Health Sciences Library: APA citation resource (N.B.: references are excluded from word counts). Note that you do not need to share your drawings done in the Chemistry tool, but you can discuss them if needed.
  Step 4: Interact
  To complete the activity, evaluate and categorize the work from one of your peers based on items A - E of the rubric below. Provide a rationale for your grade and comments or suggestions for improvement. To post a reply, click “Reply” on a particular discussion, write your feedback, then click “Post to forum.” You can use the list below as an example:
  Item A is .…. because…. My suggestions for improvement are….
  Item B is .…. because…. My suggestions for improvement are….
  Item C is .…. because…. My suggestions for improvement are….
  Item D is .…. because…. My suggestions for improvement are….
  Item E is .…. because…. My suggestions for improvement are….
- Quiz: Module 7
  To access the quiz, click on the name of the quiz provided above. On the following screen, click the attempt quiz button to respond to the questions.
Module 8: Alcohol - Structure, Synthesis, Reactivity

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