Pinacol Rearrangement of asymmetrical diol

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In summary, the conversation discusses the pinacol rearrangement of 1,1-diphenylethane-1,2-diol and how to determine which hydroxyl group is protonated. The approach of protonating the hydroxyl group on carbon 1 is correct, as it yields a stable tertiary carbocation. However, for the piñacolada to become piñacologne, the hydroxyl group on carbon 2 must undergo rearrangement.
  • #1
qkfqkekr
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Homework Statement
write down the mechanism of pinacol arrangement of the following diols
Relevant Equations
none
I have a question for the first part a), pinacol rearrangement of 1,1-diphenylethane-1,2-diol (did I name that right..?).
How would you know if protonation takes place on the hydroxyl molecule attached to carbon 1 or carbon 2?
My guess is that the hydroxyl group at carbon 1 would be protonated, since leaving of the hydroxyl group (as water) will yield tertiary carbocation, which is stable.
Is this approach correct?
1628247401136.png



Thank you for your help!
 
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  • #2
qkfqkekr said:
Homework Statement:: write down the mechanism of pinacol arrangement of the following diols
Relevant Equations:: none

I have a question for the first part a), pinacol rearrangement of 1,1-diphenylethane-1,2-diol (did I name that right..?).
How would you know if protonation takes place on the hydroxyl molecule attached to carbon 1 or carbon 2?
My guess is that the hydroxyl group at carbon 1 would be protonated, since leaving of the hydroxyl group (as water) will yield tertiary carbocation, which is stable.
Is this approach correct?
View attachment 287170


Thank you for your help!
If the hydroxyl group at carbon 1 was protonated, then which group would undergo rearrangement for the piñacolada to become piñacologne? I believe it needs to be the hydroxyl group on carbon 2.
 

1. What is the Pinacol Rearrangement of asymmetrical diol?

The Pinacol Rearrangement of asymmetrical diol is a chemical reaction that involves the conversion of a diol (a molecule with two hydroxyl groups) into a carbonyl compound (a molecule with a carbon-oxygen double bond) through a rearrangement of atoms.

2. How does the Pinacol Rearrangement of asymmetrical diol occur?

The reaction typically occurs in the presence of an acid catalyst, such as sulfuric acid or hydrochloric acid. The acid protonates one of the hydroxyl groups in the diol, making it more susceptible to nucleophilic attack by the other hydroxyl group. This leads to the formation of a cyclic intermediate, which then undergoes a series of rearrangements to produce the carbonyl compound.

3. What are the applications of the Pinacol Rearrangement of asymmetrical diol?

This reaction is commonly used in organic synthesis to create a variety of carbonyl compounds, such as aldehydes, ketones, and esters. It is also used in the production of pharmaceuticals, fragrances, and other industrial chemicals.

4. What are the factors that affect the rate of the Pinacol Rearrangement of asymmetrical diol?

The rate of the reaction can be influenced by several factors, including the strength and concentration of the acid catalyst, the structure of the diol, and the solvent used. Higher temperatures can also increase the rate of the reaction.

5. Are there any limitations or challenges associated with the Pinacol Rearrangement of asymmetrical diol?

One limitation of this reaction is that it only works with asymmetrical diols, as symmetrical diols do not undergo the necessary rearrangement. Additionally, side reactions may occur, leading to the formation of unwanted byproducts. Careful control of reaction conditions and purification steps may be necessary to obtain the desired product.

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