Q76E - Organic Chemistry (Mcmurry)

Question

Would you expect p-methylphenol to be more acidic or less acidic than unsubstituted phenol? Explain. (See Problem 16-75.)

Step-by-Step Solution

Answer

The Methyl group destabilizes the negative charge intermediate and raises the value of Gibbs energy and pKa value of the molecule which makes the p-methyl phenol less than phenol.

Acidic compound

The compound is acidic in nature when its pk_a value is low and more acidic the compound will be and the gibs energy is more in negative shows show spontaneous is the compound that is more acidic.

The electron-withdrawing group stabilizes the molecule making it more acidic and the electro releasing group destabilizes the molecule making it less acidic.

p-methyl phenol acidic nature

p-methyl phenol is less acidic than unsubstituted phenol because the methyl group is the electron-donating group due to which it destabilizes the system and it raises the gibs energy and the pk_a value and we know that higher will be the pk_a value acidic strength is lowered and also the conjugate base of the p-methyl phenol is less stable which make the molecule less acidic and phenol is more acidic in nature.