Question

Rank the following in order of increasing acidity (1=least acidic .... 4=most acidic)

a. 2,3-difluorobutanoic acid
b. 4,4-difluorobutanoic acid
c. 3,3-difluorobutanoic acid
d. 3,4-difluorobutanoic acid

Answer 1

The order of increasing acidity is: 3,3-difluorobutanoic acid, 2,3-difluorobutanoic acid, 4,4-difluorobutanoic acid, and 3,4-difluorobutanoic acid.

Step-by-step explanation:

The order of increasing acidity can be determined by looking at the pKa values of the compounds. The lower the pKa value, the stronger the acid. In this case, the compounds are:

1. 3,3-difluorobutanoic acid with a pKa value of 0.52
2. 2,3-difluorobutanoic acid with a pKa value of 0.66
3. 4,4-difluorobutanoic acid with a pKa value of 2.87
4. 3,4-difluorobutanoic acid with a pKa value of 4.76

Therefore, the order of increasing acidity is:
1. 3,3-difluorobutanoic acid
2. 2,3-difluorobutanoic acid
3. 4,4-difluorobutanoic acid
4. 3,4-difluorobutanoic acid