Draw the mechanism of the reactions of steps 1 and 2

In summary, the conversation is about a task that the speaker is struggling with and needs help with. They ask for an explanation on how to draw the full mechanism and provide some details about the task. The other person suggests showing some work before getting help and the speaker agrees to do so. The speaker then shares their approach and asks for confirmation if it is correct. The other person gives some feedback and points out some minor errors but overall approves of the mechanism. The conversation ends with the speaker thanking the other person for their help.
  • #1
physicisttobe
56
13
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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  • #2
You need to show some work before we can help you. Maybe start by identifying which reagent deprotects which functional group.
 
  • #3
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
 
  • #4
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.
 
  • Like
Likes physicisttobe
  • #5
All right, thanks a lot!!
 

FAQ: Draw the mechanism of the reactions of steps 1 and 2

What is meant by the "mechanism" of a reaction?

The mechanism of a reaction refers to the step-by-step sequence of elementary reactions by which overall chemical change occurs. It details the movement of electrons, the breaking and forming of bonds, and the intermediates formed during the reaction process.

How do you determine the mechanism of a reaction?

Determining the mechanism of a reaction typically involves a combination of experimental observations and theoretical calculations. Techniques such as spectroscopy, kinetic studies, and isotopic labeling can provide insights into the intermediates and transition states. Computational chemistry methods can also be used to model and predict mechanisms.

What are the common symbols used in drawing reaction mechanisms?

Common symbols include curved arrows to indicate the movement of electron pairs, double-headed arrows for resonance structures, and various notation for intermediates such as radicals (•), carbocations (+), and carbanions (-). Lone pairs of electrons and formal charges are also often shown for clarity.

Why is it important to understand the mechanism of a reaction?

Understanding the mechanism of a reaction is crucial for predicting the outcome of the reaction, optimizing reaction conditions, and designing new reactions. It helps chemists understand how and why reactions occur, which can lead to the development of more efficient and selective synthetic methods.

Can the mechanism of a reaction change under different conditions?

Yes, the mechanism of a reaction can change under different conditions such as temperature, pressure, solvent, and the presence of catalysts. These factors can influence the stability of intermediates and transition states, leading to different pathways and products.

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