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Homework Help: Organic chemistry acetal reaction help

  1. Oct 2, 2017 #1
    <Moderator's note: Moved from a technical forum and thus no template.>

    OChem Question:
    o7XLLLJ.jpg


    My Answer:

    upload_2017-10-2_16-43-9.png

    Not sure if this is correct. Anyone?
     

    Attached Files:

    Last edited by a moderator: Oct 2, 2017
  2. jcsd
  3. Oct 2, 2017 #2

    TeethWhitener

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    What's your reasoning for the cyclohexanol hosting an acetal carbon?

    Edit: is this homework? If so, it belongs in the homework forums.
     
  4. Oct 2, 2017 #3
    Cyclohexanol is larger. I think it could go either way. Are there major and minor products here? Sorry I thought this was the homework forum. How do I move this thread?
     
  5. Oct 2, 2017 #4

    TeethWhitener

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    I asked the mods to migrate the thread. Meanwhile, can you tell me how to make an acetal? What functional groups are required?
     
  6. Oct 2, 2017 #5
    Thank you so much. You need alcohols, a leaving group (like H2O) and acid catalyst to make an acetal.
     
  7. Oct 2, 2017 #6

    TeethWhitener

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    Alcohol and??? What other organic functionality do you need?
     
  8. Oct 2, 2017 #7
    Carbonyl group?
     
  9. Oct 2, 2017 #8

    TeethWhitener

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    Yes. If you have a carbonyl group, what happens if you add one equivalent of alcohol? (Formally, ignoring equilibrium considerations) Do you get an acetal right off the bat?
     
  10. Oct 2, 2017 #9
    You will get a hemiacetal. But I thought you need oxidizing agents to turn alcohols into carbonyls? How do we get a carbonyl in this case with only sulfuric acid?
     
  11. Oct 2, 2017 #10

    TeethWhitener

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    You're getting ahead of yourself. Look at your original problem and tell me what functionalities you have.
    Edit: hemiacetal is right (and is the important part). The rest of the post veers off the path a little.
     
  12. Oct 2, 2017 #11
    I see. So the hemiacetal is the upload_2017-10-2_17-44-23.png . and so it will form a carbonyl after the H2O group leaves and then the cyclohexanol will attack to the carbonyl carbon?

    Do you know how to name the upload_2017-10-2_17-44-23.png molecule?
     
  13. Oct 2, 2017 #12

    TeethWhitener

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    You've added a step. "Hemiacetal" literally means "half an acetal." Meaning you're already halfway to an acetal. Take another stab at it.
     
  14. Oct 2, 2017 #13
    I am not sure what you mean. I described these steps here I think:

    upload_2017-10-2_17-51-52.png
     
  15. Oct 2, 2017 #14

    TeethWhitener

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    Ah I see what you're saying. That's an oxonium, not a carbonyl. Yes, these are the steps you want. So what's your final product?
     
  16. Oct 2, 2017 #15
    This: upload_2017-10-2_17-59-22.png
     
  17. Oct 2, 2017 #16

    TeethWhitener

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  18. Oct 2, 2017 #17
    Thank you so much!!!
     
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