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In the following reaction, only one of the hydroxyl groups in D reacts under the given conditions:

 

enter image description here

I was wondering which OH group reacts and why? Also I have been trying to determine the structure of E based on which hydroxyl group reacts.

My thoughts are that OH in the side group can react via SN2 with the reactants, but the OH right adjacent to the ether O can react leaving a carbocation that can be stabilised by lone pair from O. This would mean SN1 and a completely different product.

Can someone please explain the correct mechanism?

In the following reaction, only one of the hydroxyl groups in D reacts under the given conditions:

 

enter image description here

I was wondering which OH group reacts and why? Also I have been trying to determine the structure of E based on which hydroxyl group reacts.

My thoughts are that OH in the side group can react via SN2 with the reactants, but the OH right adjacent to the ether O can react leaving a carbocation that can be stabilised by lone pair from O. This would mean SN1 and a completely different product.

Can someone please explain the correct mechanism?

In the following reaction, only one of the hydroxyl groups in D reacts under the given conditions:

enter image description here

I was wondering which OH group reacts and why? Also I have been trying to determine the structure of E based on which hydroxyl group reacts.

My thoughts are that OH in the side group can react via SN2 with the reactants, but the OH right adjacent to the ether O can react leaving a carbocation that can be stabilised by lone pair from O. This would mean SN1 and a completely different product.

Can someone please explain the correct mechanism?

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Gaurang Tandon
Gaurang Tandon
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How to determine the most reactive hydroxyhydroxyl group of α-ᴅ-glucopyranose?

So here's the problem:

In the following reaction, only one of the hydroxyl groups in D reacts under the given conditions:

enter image description here

enter image description here

I was wondering which OH group reacts and why? Also I have been trying to determine the structure of E based on which hydroxyl group reacts.

My thoughts are that OH in the side group can react via SN2SN2 with the reactants, but the OH right adjacent to the ether O can react leaving a carbocation that can be stabilised by lone pair from O. This would mean SN1SN1 and a completely different product.

Can someone please explain the correct mechanism?

How to determine the most reactive hydroxy group of α-ᴅ-glucopyranose?

So here's the problem:

enter image description here

I was wondering which OH group reacts and why? Also I have been trying to determine the structure of E based on which hydroxyl group reacts.

My thoughts are that OH in the side group can react via SN2 with the reactants, but the OH right adjacent to the ether O can react leaving a carbocation that can be stabilised by lone pair from O. This would mean SN1 and a completely different product.

Can someone please explain the correct mechanism?

How to determine the most reactive hydroxyl group of α-ᴅ-glucopyranose?

In the following reaction, only one of the hydroxyl groups in D reacts under the given conditions:

enter image description here

I was wondering which OH group reacts and why? Also I have been trying to determine the structure of E based on which hydroxyl group reacts.

My thoughts are that OH in the side group can react via SN2 with the reactants, but the OH right adjacent to the ether O can react leaving a carbocation that can be stabilised by lone pair from O. This would mean SN1 and a completely different product.

Can someone please explain the correct mechanism?

deleted 20 characters in body; edited title
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user7951
user7951

Determining How to determine the most reactive hydroxylhydroxy group of α-ᴅ-glucopyranose?

So here's the problem:

![enter image description here][1]enter image description here

I was wondering which OH group reacts and why? Also I have been trying to determine the structure of E based on which hydroxyl group reacts.

My thoughts are that OH in the side group can react via SN2 with the reactants....but, but the OH right adjacent to the ether O can react leaving a carbocation that can be stabilised by lone pair from O. This would mean SN1 and a completely different product.

Can someone please explain the correct mechanism? Thank you very much! [1]: https://i.sstatic.net/gzUC0.jpg

Determining the most reactive hydroxyl group?

So here's the problem:

![enter image description here][1]

I was wondering which OH group reacts and why? Also I have been trying to determine the structure of E based on which hydroxyl group reacts.

My thoughts are that OH in the side group can react via SN2 with the reactants....but the OH right adjacent to the ether O can react leaving a carbocation that can be stabilised by lone pair from O. This would mean SN1 and a completely different product.

Can someone please explain the correct mechanism? Thank you very much! [1]: https://i.sstatic.net/gzUC0.jpg

How to determine the most reactive hydroxy group of α-ᴅ-glucopyranose?

So here's the problem:

enter image description here

I was wondering which OH group reacts and why? Also I have been trying to determine the structure of E based on which hydroxyl group reacts.

My thoughts are that OH in the side group can react via SN2 with the reactants, but the OH right adjacent to the ether O can react leaving a carbocation that can be stabilised by lone pair from O. This would mean SN1 and a completely different product.

Can someone please explain the correct mechanism?

Tweeted twitter.com/#!/StackChemistry/status/611292827180515329
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justbehappy
justbehappy
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