Predict which member of each pair will be more acidic. Explain your answers.

(a) methanol or tert-butyl alcohol

(b)2-chloropropan-1-ol or 3-chloropropan-1-ol

(c)2-chloroethanol or 2,2-dichloroethanol

(d)2,2-dichloropropan-1-ol or 2,2-difluoropropan-1-ol

Alcohols constitute an important compound in organic chemistry.They are employed for several purposes like perfume preparation, sweeteners, manufacture of other compounds, etc.

The alcohol’s hydroxyl proton is weakly acidic. The hydroxyl proton can be removed using a strong base to create an alkoxide ion.

(a)The molecule possessing lesser substitution will have more acidity. In the compounds methanol and tert-butyl alcohol, methanol has more acidity as it is less substituted than tert-butyl alcohol.

(b)The electron withdrawing chlorine atom is near to the OH group in 2-Chloropropan-1-ol than in 3-chloropropan-1-ol. Hence, 2-chloropropan-1-ol is more acidic than 3-chloropropan-1-ol .

(c)The molecule, 2-2-Dichloroethanol comprise two electron withdrawing chlorine groups which increase acidity. The number of electron withdrawing groups in 2-chloroethanol is one. Hence, 2, 2-Dichloroethanol is more acidic than 2-chloroethanol.

(d)The alcohol comprising a stronger electron-withdrawing group is more acidic. The electron-withdrawing group, fluorine in 2, 2-difluoropropan-1-ol is more electronegative than the electron-withdrawing group, chlorine in 2, 2-dichloropropan-1-ol. Hence, 2, 2-difluoropropan-1-ol is more acidic than 2, 2-dichloropropan-1-ol.