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Topic: Do not Understand this Mechanism? - Silyl Ethers as a Protecting Group  (Read 3628 times)

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Offline disneygurl2010

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I'm having trouble understanding this reaction and what is going on through the steps.  I just know that Silyl Ethers have certain protecting groups that are used when a molecule has more than 1 functional group (to prevent one from reacting) & general info about TMS but I'm still confused =/

Offline discodermolide

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Re: Do not Understand this Mechanism? - Silyl Ethers as a Protecting Group
« Reply #1 on: February 05, 2012, 03:24:38 PM »
I'm having trouble understanding this reaction and what is going on through the steps.  I just know that Silyl Ethers have certain protecting groups that are used when a molecule has more than 1 functional group (to prevent one from reacting) & general info about TMS but I'm still confused =/

What is confusing you? It is a pretty straightforward series of steps.
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Offline disneygurl2010

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Re: Do not Understand this Mechanism? - Silyl Ethers as a Protecting Group
« Reply #2 on: February 05, 2012, 03:28:20 PM »
I guess just the whole concept of what this actually is.  I learned Sn1 and Sn2 last unit and alcohols.  This is a new unit and I guess I'm just not making sense of how this reaction is impt

Offline discodermolide

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Re: Do not Understand this Mechanism? - Silyl Ethers as a Protecting Group
« Reply #3 on: February 05, 2012, 04:31:31 PM »
I guess just the whole concept of what this actually is.  I learned Sn1 and Sn2 last unit and alcohols.  This is a new unit and I guess I'm just not making sense of how this reaction is impt

Well you are trying to alkylate an acetylene in the presence of another reactive group, under these conditions, So what does one do? One protects the other reactive group so that it does not interfere in the desired reaction.
Does that help?
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Offline DrCMS

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Re: Do not Understand this Mechanism? - Silyl Ethers as a Protecting Group
« Reply #4 on: February 06, 2012, 04:36:17 AM »
I guess just the whole concept of what this actually is.  I learned Sn1 and Sn2 last unit and alcohols.  This is a new unit and I guess I'm just not making sense of how this reaction is impt

As discodermolide has said the starting material has more than 1 reactive group. 
What would happen to your stating material, 4-Pentyn-1-ol, if you went straight to the 2nd step reaction without protecting the alcohol?

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