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Chapter 44: 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 CH3CH2OH is the hydrogen in the OH group.

Step by step solution

01

Identify the hydrogen atoms in the compound

In CH3CH2OH, there are two types of hydrogen atoms present. Three hydrogen atoms are in methyl group CH3, two hydrogen atoms are in methylene group CH2 and one hydrogen atom is in the hydroxyl group OH.
02

Consider the stability of the conjugate base

After losing a proton (H+), the remaining part of the acid is termed the conjugate base. The hydrogen atom in the hydroxyl group OH can dissociate to leave a negative charge on oxygen, forming a hydroxide ion OH-. Oxygen being highly electronegative can easily stabilize this negative charge.
03

Compare the acidity of hydrogen atoms

The hydrogen atoms in the methyl and methylene groups, after dissociation, would leave a negative charge on the carbon atom. Carbon, being less electronegative than oxygen, cannot stabilize the charge as effectively as oxygen. Therefore the hydrogen atom in OH group is more acidic than those in the CH3 and CH2 groups.

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Most popular questions from this chapter

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

Which hydrogen atom is the most acidic hydrogen atom in HCOOH?

The H-X bond strength decreases in the series HF, HCl, HBr, HI. Explain this trend in terms of the molecular structure of the molecules.

What structural features or atomic property causes the partial charge on the acidic hydrogen to increase in the series \(\mathrm{CH}_{3} \mathrm{COOH}, \quad \mathrm{CH}_{2} \mathrm{ClCOOH}\), \(\mathrm{CHCl}_{2} \mathrm{COOH}, \mathrm{CCl}_{3} \mathrm{COOH} ?\)
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