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Alcohols as Nucleophiles and Electrophiles

Which is true...

Question

Which is true about the acidic character of hydroxyl groups of sugars and hydroxyl group of an alcohol ?

A

The OH's of sugars are more acidic than that of a typical alcohol

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B

The OH's of sugars are less acidic than that of a typical alcohol

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C

Both have similar acidic character

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D

The OH's of sugars are netral while that of an alcohol is acidic

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Solution

The correct option is A
The OH's of sugars are more acidic than that of a typical alcohol

The OH's of sugars are more acidic than that of a typical alcohol because of their mutual electron withdrawing inductive effect.

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Similar questions

Q. Phenols are compounds in which a hydroxyl group is bonded directly to an

s p^{2}

hybridized carbon atom of an aromatic ring. It is more acidic than an alcohol, but less acidic than a carboxylic acid. It is even less acidic than carbonic acid but more acidic than water. Thus, phenol is unable to protonate

H C O_{3}^{-}

anion but easily protonates

O H^{-}

O H^{-}

group activates the benzene ring so much that electrophilic substitution takes place readily.

The correct order of acidity of the following substituted phenols is:

Q. Both phenol and alcohol contains -OH group, but still phenol is more acidic than alcohol. Explain why?

- O H

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Q. Carboxylic acids are more acidic than phenol and alcohol because of

Intermolecular hydrogen bonding

Formation of dimers

Highly acidic hydrogen

Resonance stabilization of their conjugate base

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