Arrange the following in the order of increasing acidity. List the most acidic last.
CH3OH
CH3CO2H
CH3CH2CH2CH3
If given a table of acids and their pKas, how do you determine which acid is stronger, especially when the table does not have the compounds that are above listed on the table?
Here is a chart of the table given.
HCl pKa= -7. CH3CO2H pKa= 4.8. H2O pKa= 15.7. CH3CH2OH pKa= 16. CHCH pKa= 25. H2 pKa= 35. H2NH pKa= 38. CH2CH2 pKa= 44. CH3H pKa=50
CH3OH is methanol, containing – OH group
CH3CO2H is acetic acid containing –COOH group
CH3CH2CH2CH3 is butane, which is an alkane
The table does not have the compounds that are above listed, but on the table there are compounds, which have same functional group. For example on the table there is ethanol with pKa = 16
PKa of alcohol group is 16, so pKa of methanol =16
PKa of CH3H is 50 (given in table) so, pKa of alkanes are 50. PKa of CH3CH2CH2CH3 is 50
Compound with lower PKa is more acidic. CH3CO2H (PKa= 4.8) has lower PKa than CH3OH and CH3CH2CH2CH3 , so it is more acidic than CH3OH and CH3CH2CH2CH3 and CH3OH has lower PKa than CH3CH2CH2CH3 , so it is more acidic than CH3CH2CH2CH3 .
The order of increasing acidity of compounds is
Least acidic CH3CH2CH2CH3 < CH3OH < CH3CO2H more acidic
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