Section: Module 9: Lesson 2: Retrosynthetic Analysis | Organic Chemistry 1 | NextGenU.org

  • Student Learning Outcomes:
    Upon completion of this lesson, you will be able to:
    • Use retrosynthetic analysis to design efficient multi-step syntheses involving organic molecule intermediates or final products.
    • Predict nomenclature, reactions, mechanisms, and synthesis design to reaction conditions and reagents.
    • Determine the structure of an unknown organic compound using clues provided by products of reactions.
    • Determine the stereochemistry of a starting organic compound given reactants and the product stereochemistry/ selectivity.
    Approximate time required for the readings for this lesson (at 144 words/minute): 2 hours and 35 minutes.

    Click here to start this lesson

    • Required Learning Resources and Activities
    • Read the entire webpage. (4 minutes)

      Kwantlen Polytechnic University - 2021

    • Watch the entire video. (6 minutes)

      Oxford Academic (Oxford University Press) - 2013

    • General Instructions

      In this activity, you will be given a series of questions. These questions will involve retrosynthetic analysis and investigating stereochemistry and chemoselectivity. 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 retrosynthetic analysis, chemoselectivity, and stereoselectivity.

      Step 2 - Respond

      Answer the following questions:

      1. Explain the method/steps you would use to plan a multi-step synthesis. Are any steps more important than others? Why?

      2. Explain the importance of considering chemoselectivity and stereoselectivity when planning a synthesis and provide an example of a reaction that highlights the importance of these considerations.

      3. Design a synthetic route for the following product and explain the mechanism involved:

        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 9

      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 4/5

      Not available unless: The activity Quiz: Module 8 is marked complete