Section: Module 5: Lesson 7: Reaction Rates of Substitution and Elimination Reactions | Organic Chemistry 1 | NextGenU.org

  • 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

    • Required Learning Resources and Activities
    • Read the entire section. (10 minutes)

      Kwantlen Polytechnic University

    • 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:

      1. What does the energy profile diagram below tell us about the reaction between CH3Br and OH- ?

        Use the following questions to prompt your discussion:

        1. Is this SN1 or SN2?

        2. What does it tell us about the energy of the products and reactants?

        3. What does T.S. represent? What is its significance?

        4. Explain the steps of the reaction mechanism that would be involved. You can practice drawing the mechanism in the chemistry tool.

      2. 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:

        1. Is this SN1 or SN2?

        2. What does it tell us about the energy of the products and reactants?

        3. What is “intermediate”? What is its significance?

        4. Explain the steps of the reaction mechanism that would be involved. You can practice drawing the mechanism in the chemistry tool.

      3. Name and describe the mechanism for the reaction below. You can practice drawing the mechanism in the chemistry tool.


      4. Examine the two reactions presented below and answer the questions that follow.

        1. Distinguish which equation follows the Hofmann rule and which follows Zaitsev’s rule with a brief explanation of your reasoning.

        2. What are the conditions needed for each reaction to follow its respective rule?

        3. 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….

      OPTIONAL Step 5: Interact (10 minutes)

      If you would like to, you can reply to your peers' posts in a respectful and professional manner. Ensure that your post engages your peers' ideas by including a reflection on their comments, sharing ideas of other potential difficulties and parties involved, or asking thought-provoking questions. If a peer comments on your posting, please reply. To post a reply, click “Reply” on a particular discussion, write your feedback and then click on “Post to forum.”



    • quiz icon
      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.

      TO PASS THIS QUIZ YOU MUST OBTAIN A SCORE OF 80%.

      Not available unless: The activity Quiz: Module 4 is marked complete