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Ch. 2 - Acids and Bases; Functional Groups
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 2 - Acids and Bases; Functional GroupsProblem 31e-h
Chapter 2, Problem 31e-h

Which of the following pure compounds can form hydrogen bonds? Which can form hydrogen bonds with water? Which ones do you expect to be soluble in water?
e. CH3(CH2)3CH3
f. CH2=CH—CH2CH3
g. CH3COCH3
h. CH3CH2COOH

Verified step by step guidance
1
Identify the functional groups present in each compound. Hydrogen bonding typically occurs with molecules containing N-H, O-H, or F-H bonds.
For compound e (CH3(CH2)3CH3), recognize that it is a hydrocarbon (alkane) with no polar groups, thus it cannot form hydrogen bonds.
For compound f (CH2=CH—CH2CH3), note that it is an alkene with no polar groups, so it cannot form hydrogen bonds.
For compound g (CH3COCH3), identify the carbonyl group (C=O). While the compound itself cannot form hydrogen bonds, it can interact with water through hydrogen bonding due to the oxygen's lone pairs.
For compound h (CH3CH2COOH), recognize the carboxylic acid group (COOH), which can form hydrogen bonds both within itself and with water due to the O-H bond. This increases its solubility in water.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Hydrogen Bonding

Hydrogen bonding occurs when a hydrogen atom is covalently bonded to a highly electronegative atom, such as oxygen, nitrogen, or fluorine, allowing it to interact with lone pairs on other electronegative atoms. This interaction is crucial for determining solubility and intermolecular forces in compounds.
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Solubility in Water

Solubility in water is influenced by a compound's ability to form hydrogen bonds with water molecules. Polar compounds with functional groups like -OH, -NH, or -COOH can interact with water, increasing solubility, whereas nonpolar compounds with long hydrocarbon chains are typically less soluble.
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Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for characteristic chemical reactions. In organic chemistry, groups like alcohols (-OH), carboxylic acids (-COOH), and ketones (C=O) can influence a compound's ability to form hydrogen bonds and affect its solubility in water.
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Related Practice
Textbook Question

For each of the following compounds,

1. draw the Lewis structure.

2. show how the bond dipole moments (and those of any nonbonding pairs of electrons) contribute to the molecular dipole moment.

3. estimate whether the compound will have a large, small, or zero dipole moment.

e.

659
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Textbook Question

Predict which member of each pair is more soluble in water. Explain your prediction.

(e)

(f)

1369
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Textbook Question

Which of the following pure compounds can form hydrogen bonds? Which can form hydrogen bonds with water? Which ones do you expect to be soluble in water?

a. (CH3CH2)2NH

b. (CH3CH2)3N

c. CH3CH2CH2OH

d. (CH3CH2CH2)2OH

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Textbook Question

Predict which member of each pair is more soluble in water. Explain your prediction.

(c)

(d)

1189
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Textbook Question

Sulfur dioxide has a dipole moment of 1.60 D. Carbon dioxide has a dipole moment of zero, even though C―O bonds are more polar than S―O bonds. Explain this apparent contradiction.

5340
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Textbook Question

Predict which member of each pair is more soluble in water. Explain your prediction.

(a)

(b)

1471
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