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

Since alcohols contain the hydroxyl group, they are capable of forming hydrogen bonds with other compounds like water. 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.

Which is the best suitable protecting group for alcoholic Oh?

Acetal Formation The acetal function is a very suitable protecting group for alcohols under basic conditions, but is not useful under acidic conditions because acetals are not stable to acids: An excellent reagent to form acetals is the unsaturated cyclic ether, 16.

Are Phenols and alcohols differs?

The alcohols are a class of organic compounds that hold at least one hydroxyl functional group that is attached to a carbon atom. Phenols, on the other hand, are organic compounds consisting of a hydroxyl group which is attached to an aromatic system of hydrocarbons (arene).

How do Phenols differ from alcohols in terms of structure and properties?

Compounds in which an OH group is attached directly to an aromatic ring are designated ArOH and called phenols. Phenols differ from alcohols in that they are slightly acidic in water. They react with aqueous sodium hydroxide (NaOH) to form salts.

Why is phenol stronger acid than ethanol?

Phenoxide ion is aromatic and can undergo resonance but ethoxide ion can’t. Phenol is more acidic than that of ethanol because phenoxide ion is stabilized through delocalisation. An acid loses H+ ions in water. When phenol loses an H+ ion, the ion formed is known as phenoxide ion.

Why are phenols more acidic than alcohols and water?

Phenols have unique properties and are not classified as alcohols. They have higher acidities due to the aromatic ring’s tight coupling with the oxygen and a relatively loose bond between the oxygen and hydrogen.

Is OH a strong base or nucleophile?

So, strong bases — substances with negatively charged O, N, and C atoms — are strong nucleophiles. Examples are: RO⁻, OH⁻, RLi, RC≡C:⁻, and NH₂⁻. Some strong bases are poor nucleophiles because of steric hindrance.

Which of the following is used for protection of free OH group?

Dimethoxytrityl, [bis-(4-methoxyphenyl)phenylmethyl] (DMT) – Removed by weak acid. DMT group is widely used for protection of 5′-hydroxy group in nucleosides, particularly in oligonucleotide synthesis.

How can we protect phenol?

Ethers are the most widely used protective groups for phenols and in general they are more easily cleaved than the analogous ethers of simple alcohols. Esters are also important protective groups for phenols, but are not as stable to hydrolysis as the related alcohol derivatives.