Acid Strength of 1-Fluoroethanol & 1-Chloroethanol

  • Thread starter bomba923
  • Start date
  • Tags
    Acid
In summary, 1-Fluoroethanol (CH3CH2FO) and 1-Chloroethanol (CH3CH2Cl) are two molecules with a similar chemical structure, both containing a hydroxyl group (-OH) attached to a carbon atom. However, the difference in their acid strength is due to the electronegativity of the halogen atoms attached to the carbon atom, with the fluorine atom in 1-Fluoroethanol being more electronegative than the chlorine atom in 1-Chloroethanol. This results in 1-Fluoroethanol being a stronger acid, with a pKa value of 10.2 compared to 1-Ch
  • #1
bomba923
763
0
Is 1-fluoroethanol significantly more acidic than regular ethanol?

(Not just "slightly" more acidic)

What about 1-chloroethanol? Is it significantly more acidic than regular ethanol?

(see the attached image for structures of these molecules)
 

Attachments

  • acidq.GIF
    acidq.GIF
    1.2 KB · Views: 691
Chemistry news on Phys.org
  • #2
1-chloroethanol isn't stable. It will decompose into acetaldehyde and HCl. You might be able to produce fleeting amounts of it in the gas phase, but it probably wouldn't stick around long enough to measure the pKa.

For what it's worth, 2-flouroethanol is only moderately more acidic than ethanol (pKas of 14.42 and 15.18, respectively).
 
  • #3
Hm, I see / /

~Thanks for the quick response!
 

Related to Acid Strength of 1-Fluoroethanol & 1-Chloroethanol

What is the chemical structure of 1-Fluoroethanol & 1-Chloroethanol?

1-Fluoroethanol has a chemical formula of CH3CH2FO and 1-Chloroethanol has a chemical formula of CH3CH2Cl. Both molecules have a hydroxyl group (-OH) attached to a carbon atom, with a fluorine atom in 1-Fluoroethanol and a chlorine atom in 1-Chloroethanol.

What is the difference between 1-Fluoroethanol & 1-Chloroethanol in terms of acid strength?

The strength of an acid is determined by its ability to donate a proton (H+) in a solution. In this case, 1-Fluoroethanol is a stronger acid than 1-Chloroethanol because the fluorine atom in 1-Fluoroethanol is more electronegative than the chlorine atom in 1-Chloroethanol. This makes the hydrogen atom in 1-Fluoroethanol more acidic and easier to donate.

How does the structure of 1-Fluoroethanol & 1-Chloroethanol affect their acid strength?

The difference in acid strength between 1-Fluoroethanol and 1-Chloroethanol is due to the electronegativity of the halogen atoms attached to the carbon atom. The more electronegative the atom, the more stable the conjugate base will be after donating a proton, making the acid stronger. In this case, the fluorine atom in 1-Fluoroethanol is more electronegative than the chlorine atom in 1-Chloroethanol, resulting in a stronger acid.

How is the acid strength of 1-Fluoroethanol & 1-Chloroethanol measured?

The acid strength of a molecule is measured by its pKa value, which is the negative logarithm of the acid dissociation constant (Ka). A lower pKa value indicates a stronger acid. According to experimental data, the pKa value of 1-Fluoroethanol is 10.2 and the pKa value of 1-Chloroethanol is 13.5, confirming that 1-Fluoroethanol is a stronger acid.

What are the potential applications of 1-Fluoroethanol & 1-Chloroethanol in the field of chemistry?

1-Fluoroethanol and 1-Chloroethanol can both be used as solvents in various chemical reactions. They can also be used as starting materials for the synthesis of other compounds, such as esters and ethers. Additionally, 1-Fluoroethanol is commonly used in the production of pharmaceuticals and agrochemicals due to its strong acid properties and ability to form stable hydrogen bonds.

Similar threads

Replies
6
Views
1K
Replies
8
Views
961
Replies
1
Views
1K
  • Chemistry
Replies
8
Views
1K
Replies
1
Views
1K
  • Chemistry
Replies
4
Views
944
  • Chemistry
Replies
2
Views
899
Replies
16
Views
2K
Replies
1
Views
989
Replies
1
Views
2K
Back
Top