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Chapter 46: Problem 11

Which hydrogen atom is the most acidic hydrogen atom in \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) ?

Short Answer

Expert verified
The most acidic hydrogen atom in the compound \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) is the hydrogen in the \(OH\) group.

Step by step solution

01

Identifying the Hydrogen in the OH group

Firstly, consider the lone hydrogen atom in the \(OH\) group. When this hydrogen is removed (donated as a proton in a Br酶nsted-Lowry acid-base reaction) a hydroxide ion (OH-) or alkoxide ion would be formed. Alkoxide ions are resonance-stabilized; that means that the negative charge is delocalized, which increases the stability of the ion.
02

Identifying the Hydrogens in the CH3 and CH2 groups

By considering the hydrogens attached to the carbon atoms, it can be noticed that when these hydrogens are removed, the resulting carbon ions are not stabilized. Carbon is less electronegative than oxygen, meaning that it is less likely to accept the negative charge that results from the removal of a hydrogen atom.
03

Compare the Acidity of the Identified Hydrogen Atoms

By comparing the stability of the resulting anions, it is clear that the hydrogens attached to carbon atoms are less acidic compared to the hydrogen in the hydroxyl group. This is a result of the greater stability of the alkoxide ion compared to the carbon ions.

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Most popular questions from this chapter

Based on your analysis above, which do you expect to be the stronger acid, \(\mathrm{NH}_{4}^{+}\) or \(\mathrm{PH}_{4}^{+} ?\) Explain your reasoning.

Which hydrogen atom is the most acidic hydrogen atom in \(\mathrm{CH}_{3} \mathrm{COOH}\) ?

What structural feature accounts for the decrease in the partial charge on the acidic hydrogen in the series HOCl, HOBr, HOI?

a) Which hydrogen in \(\mathrm{CH}_{3} \mathrm{COOH}\) is the acidic hydrogen? b) Which hydrogen in \(\mathrm{CCl}_{3} \mathrm{COOH}\) is the acidic hydrogen?

Why does the partial charge on the acidic hydrogen increase in the series \(\mathrm{CH}_{3} \mathrm{COOH}, \mathrm{CH}_{2} \mathrm{ClCOOH}, \mathrm{CHCl}_{2} \mathrm{COOH}, \mathrm{CCl}_{3} \mathrm{COOH} ?\)
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