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Chapter 2: Q. 2.77 (page 90)

Which H atom in vitamin C (ascorbic acid) is most acidic?

Short Answer

Expert verified

The most acidic proton gives more resonance stabilization through the delocalization of stable carbanion.

Step by step solution

01

Acidic proton

The most acidic proton gives more resonance stabilization through the delocalization of stable carbanion.

02

Delocalization of carbanion

A carbanion (bearing a negative charge) formed by the abstraction of an acidic proton transfers its electrons to the adjacent empty orbital (delocalization) and forms resonance structures.

The more the resonance structures, the more is the stability of the compound.

Therefore, the compound readily releases its proton to get stabilized by the resonance.

03

Explanation

The OH bonded with the alkene undergoes delocalization and forms three resonance stabilized structures through carbanion's formation after the proton's abstraction.

Therefore, this OH group has the most acidic hydrogen.

Formation of resonance structures

The other three -OH groups show their resonance stabilized structures as

Formation of resonance structures

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Most popular questions from this chapter

Compounds like amphetamine that contain nitrogen atoms are protonated by the HCl in the gastric juices of the stomach, and the resulting salt is then deprotonated in the basic environment of the intestines to regenerate the neutral form. Write proton transfer reactions for both of these processes. In which form will amphetamine pass through a cell membrane?

What is the conjugate base of each acid?

a. HCO3-

b.

c.

d.

Draw the product formed when the Lewis acid (CH3CH2)3C+reacts with each Lewis base:

role="math" localid="1649304251552" (a)CH3OH;(b)(CH3)2O;(c)(CH3)2NH.

Rank the compounds in each group in order of increasing acidity.

a.

b.

c.

Classify each compound as a Lewis base, a Br酶nsted -Lowry base, both or neither.

a.

b.

c.

d.
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