Section: Module 4: Lesson 4: Stereochemistry for Halogenation of Alkanes | Organic Chemistry 1 | NextGenU.org

  • 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

    • Required Learning Resources and Activities
    • Read the entire section. (5 minutes)

      Kwantlen Polytechnic University - 2021

    • Read the entire section. (2 minutes)

      Kwantlen Polytechnic University - 2021

    • 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:

      1. 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.


      2. 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.

      3. 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….

      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 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.

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

      Not available unless: The activity Quiz: Module 3 is marked complete