Convert but-2-yne to 2,2,3-trichlorobutane

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In summary, the conversation discusses the process of converting but-2-yne to 2,3-dichlorobutane and the correct way to add a third chlorine atom to the structure. It is determined that using 1.5 moles of Cl2 would result in a mixture of products and the correct approach would be to add an H-atom and Cl-atom across the double bond. The order of reactions is also discussed, with consideration given to electronegativity. It is determined that the addition of HCl should be done first, followed by Cl2.
  • #1
KurtWagner
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Homework Statement



Show by means of equations how you could convert but-2-yne to 2,2,3-trichlorobutane


The Attempt at a Solution



So, as far as I know, to make 2,3-dichlorobutane, all that is required is the addition of one mole of Cl2 in the presence of an organic solvent.

My query is how to add just one more Cl to the structure.

My first thought is to use 1.5 moles of Cl2 for each mole of but-2-yne:

2 C4H6 + 3Cl2 → C4H7Cl3

Is this the correct way to do this?
 
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  • #2
No, you will get 2,2,3,3-tetrachlorobutane mixed with 2,3-dichlorobut-2-ene this way.
 
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  • #3
KurtWagner said:
So, as far as I know, to make 2,3-dichlorobutane, all that is required is the addition of one mole of Cl2 in the presence of an organic solvent.

No, you would get 2,3-dichlorobut-2-ene if you do that with but-2-yne. Now you need to add an H-atom and Cl-atom across the double bond. Can you think of a reaction which does that?
 
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  • #4
Pranav-Arora said:
No, you would get 2,3-dichlorobut-2-ene if you do that with but-2-yne. Now you need to add an H-atom and Cl-atom across the double bond. Can you think of a reaction which does that?

So I need one mole of Cl2 and one of HCl?

Oh, and yeah I should have said 'ene', thanks.
 
  • #5
KurtWagner said:
So I need one mole of Cl2 and one of HCl?

Only one mole of HCl. :)
 
  • #6
Thanks
 
  • #7
One reaction then another. Impeccable! The easy part is done! But is there a best order, and if so which?
 
  • #8
Does the answer to the order have to do with electronegativity?
 
  • #9
KurtWagner said:
Does the answer to the order have to do with electronegativity?

I think so. If HCl addition is done first, the vinyl cation being formed is less stable. Cl2 addition should be done first.
 
  • #10
I don't know answers, my first question would be whether reactions conveniently stop after the first bond opening.
 

Related to Convert but-2-yne to 2,2,3-trichlorobutane

1. How can but-2-yne be converted to 2,2,3-trichlorobutane?

The conversion of but-2-yne to 2,2,3-trichlorobutane can be achieved through a series of chemical reactions involving the addition of chlorine molecules to the carbon-carbon triple bond of but-2-yne.

2. What reagents are required for this conversion?

The conversion of but-2-yne to 2,2,3-trichlorobutane typically requires the use of reagents such as chlorine gas, hydrochloric acid, and a catalyst such as iron(III) chloride.

3. What is the mechanism of this conversion?

The conversion of but-2-yne to 2,2,3-trichlorobutane follows a radical addition mechanism, where the chlorine atoms add to the carbon-carbon triple bond in a stepwise manner, forming a series of intermediates before the final product is obtained.

4. Are there any safety concerns when performing this conversion?

Yes, there are safety concerns when working with chlorine gas and hydrochloric acid, as they are corrosive and can cause irritation and damage to the skin and respiratory system. Proper safety precautions and equipment should be used when handling these reagents.

5. What is the yield of this conversion?

The yield of this conversion can vary depending on the reaction conditions and the purity of the starting materials. Generally, a high yield can be achieved if the reaction is carefully controlled and the starting materials are of good quality.

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