Draw the mechanism of the reactions of steps 1 and 2

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Discussion Overview

The discussion revolves around drawing the full mechanism for chemical reactions in steps 1 and 2, specifically focusing on the use of protecting groups and the role of Tetramethylguanidine (TMG) and monomethoxytrityl (MMT). Participants are seeking clarification and guidance on how to accurately depict these mechanisms.

Discussion Character

  • Homework-related
  • Technical explanation
  • Conceptual clarification

Main Points Raised

  • One participant requests help in drawing the full mechanism for the reactions in steps 1 and 2, indicating specific reagents and protecting groups involved.
  • Another participant suggests that the original poster should show some work and identify which reagent deprotects which functional group to facilitate assistance.
  • The original poster expresses uncertainty about their mechanism and shares their approach, seeking validation.
  • A subsequent reply acknowledges the original poster's idea but points out minor errors regarding the representation of protecting groups in the mechanism diagrams.

Areas of Agreement / Disagreement

The discussion does not reach a consensus, as participants provide feedback and corrections without establishing a definitive solution to the mechanism drawing task.

Contextual Notes

Participants note specific errors related to the representation of protecting groups, indicating that attention to detail is necessary in the mechanism drawings. There is also an acknowledgment of uncertainty regarding the correctness of the original poster's approach.

Who May Find This Useful

Students or individuals working on organic chemistry mechanisms, particularly those involving protecting groups and reaction steps.

physicisttobe
Messages
56
Reaction score
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Homework Statement
Tetramethylguanidine/monomethoxytrityl
Relevant Equations
...
Hi everyone!

There is a task that I can't solve. Can you explain me how I have to draw the full mechanism?

Draw the mechanism of the reactions of step 1 and 2. Indicate the product before step
3. (in step 2 also TMG =Tetramethylguanidine is given and instead of the
protecting group DMT was given MMT =monomethoxytrityl).
 

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You need to show some work before we can help you. Maybe start by identifying which reagent deprotects which functional group.
 
Oh yes, next time i will post all my approaches. I was a little uncertain, whether the mechanism is correct. Therefore, I did not upload anything.
But my approach looks like this. I hope it‘s correct:
55A6DE7F-8A7B-49FD-8B11-D134B8CDA8BB.jpeg
 
It looks like you have the idea. A couple of minor things: make sure the protecting groups you aren’t removing stay on the diagrams, and make sure the protecting groups you’ve already removed don’t (for instance, in the mechanism for step 2, you still have the DMT group protecting the sugar OH, which you just showed was removed in step 1). There’s one or two other little errors of that nature, but overall, the mechanism looks pretty good.
 
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Likes   Reactions: physicisttobe
All right, thanks a lot!!
 

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