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Chapter 2: Q 2-2-41 E (page 59)

TheO-H hydrogen in acetic acid is more acidic than anyhydrogens. Explain this result using resonance structures.

Short Answer

Expert verified

OH hydrogen is resonance stabilized.

Step by step solution

01

Acidic hydrogen

The hydrogen which can be more easily released from a molecule is more acidic than the one which is difficult to remove.

02

Resonating structure of acetic acid

Three resonating structures are possible for acetic acid:

Resonating structures

03

Reason for more acidic nature of OH hydrogen in acetic acid

From resonating structure, it can be seen that CH hydrogen is not stabilized by resonance. The carbocation generated will be unstable, and hence this hydrogen is hard to remove.

The hydrogen in OH is resonance stabilized. Therefore, it will generate a stable carbocation, and this hydrogen can be easily removed from the molecule. This hydrogen is, therefore, more acidic than acetic acid.

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Most popular questions from this chapter

Question: Which of the following pairs of structures represent resonance forms?

Question: Which of the following pairs of structures represent resonance forms, and which do not? Explain.

(a)

(b)

The following molecular models are representations of (a) adenine and (b) cytosine, constituents of DNA (deoxyribonucleic acid). Indicate the positions of multiple bonds and lone pairs for both, and draw skeletal structures (gray 5 C, pink 5 O, blue 5 N, ivory 5 H).

Use the electronegativity table given in Figure 2-2 to predict which bond in each of the following pairs is more polar, and indicate the direction of bond polarity for each compound.

a)H3C-CIor CI-CI

b)H3C-HorH-CI

c)HO-CH3or (CH3)3Si-CH3

d)H3C-LiorLi-OH

Thiamin diphosphate (TPP), a derivative of vitamin B1 required for glucose metabolism, is a weak acid that can be deprotonated by a base. Assign formal charges to the appropriate atoms in both TPP and its deprotonation product.
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