Answer to Question #134437 in Organic Chemistry for Jane Villanueva

Question

Why do phenols sometimes react differently from alcohols despite the presence of the same functional group?

Answer 1

However, acetic acid (CH3COOH)

(CH3​COOH) is not an alcohol despite having a hydroxyl group. This is because the carbon atom to which the hydroxyl group is attached is unsaturated, as it is double bonded with an oxygen atom. Instead, acetic acid is a carboxylic acid.

Since alcohols contain the hydroxyl group, they are capable of forming hydrogen bonds with other compounds like water. Since alkyl groups are considered to be non-polar, alcohols tend to have a higher solubility in water when the carbon chain of the substituent (R)

(R) is small. Thus alcohols like methanol or ethanol tend to mix well with water, whereas alcohols with more than four carbons (e.g. pentanol, hexanol) are considered insoluble in water.

Most alcohols are very weak acids. Though the pH of an alcohol solution is almost neutral, they are still able to react with strong bases. Phenol is relatively strong an acid compared to alkyl alcohols.