All of the following compounds can react as acids. without using a table of acidities, rank them in order of increasing acidity. explain your ranking. a. ch3ch2so3h b. ch3ch oh c. ch3ch2cooh d. ch3chcicooh e. cich ch2cooh

The increasing order of Bronsted acids is:

(b) < (c) < (e) < (d) < (a)

Explanation:

A Bronsted acid is a substance who donated protons.

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The acidity of a compound is determined by the acidity constant and every factor that stabilizes the product of the acid reaction (the anion) will contribute to increase the acidity of the compound.

First, it is necesary to identify the donor group:

(a) is -SO3H

(b) is -OH

(c), (d) and (e) is -COOH

For these groups the order of acidity is

-SO3H > -COOH > -OH

The strongest is the group -SO3H because it comes from a strong inorganic acid (H2SO4). Second is the group -COOH, carboxylic acids are the strongest organic acids because of the resonance structure of the anion at acid equilibrium, this equilibrium shifts the reaction to products favoring deprotonation. Third is the group of -OH because alcohols are weak acids.

Further, between (c), (d) and (e) it is necessary to analyze the molecule substituents. The -Cl substituent is an electronegative group that stabilizes the anion of the equilibrium because of its inductive effect. Thus, the molecule with the -Cl near to de acidic group will be more acidic. Therefore the order of acidity between these three compounds will be: (d) > (e) > (c)

Summarised all, the final answer is (b) < (c) < (e) < (d) < (a)

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