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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 5a,b
Chapter 2, Problem 5a,b

Draw the hydrogen bonding that takes place between
a. two molecules of ethanol.
b. two molecules of propylamine.

Verified step by step guidance
1
Step 1: Understand the concept of hydrogen bonding. Hydrogen bonds are a type of dipole-dipole interaction that occur between a hydrogen atom bonded to a highly electronegative atom (such as oxygen, nitrogen, or fluorine) and another electronegative atom.
Step 2: For ethanol (C₂H₅OH), identify the hydrogen bond donor and acceptor. The hydroxyl group (-OH) contains an oxygen atom that can act as a hydrogen bond acceptor, and the hydrogen atom attached to this oxygen can act as a hydrogen bond donor.
Step 3: Draw two ethanol molecules. Position them so that the hydrogen atom of the hydroxyl group in one molecule is near the oxygen atom of the hydroxyl group in the other molecule. Represent the hydrogen bond as a dashed line between the hydrogen and oxygen atoms.
Step 4: For propylamine (C₃H₇NH₂), identify the hydrogen bond donor and acceptor. The amino group (-NH₂) contains a nitrogen atom that can act as a hydrogen bond acceptor, and the hydrogen atoms attached to this nitrogen can act as hydrogen bond donors.
Step 5: Draw two propylamine molecules. Position them so that the hydrogen atom of the amino group in one molecule is near the nitrogen atom of the amino group in the other molecule. Represent the hydrogen bond as a dashed line between the hydrogen and nitrogen atoms.

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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 is a type of dipole-dipole interaction that occurs when a hydrogen atom covalently bonded to a highly electronegative atom, such as oxygen or nitrogen, interacts with another electronegative atom. This bond is weaker than covalent bonds but stronger than van der Waals forces, playing a crucial role in determining the properties of molecules like ethanol and propylamine.
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The definition of hydrogenation.

Ethanol Structure and Properties

Ethanol (C2H5OH) is an alcohol with a hydroxyl group (-OH) that can form hydrogen bonds. In ethanol, the oxygen atom is highly electronegative, allowing it to attract hydrogen atoms from other ethanol molecules, facilitating hydrogen bonding. This interaction significantly influences ethanol's boiling point and solubility in water.
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Propylamine Structure and Properties

Propylamine (C3H7NH2) is an amine with a primary amine group (-NH2) capable of forming hydrogen bonds. The nitrogen atom in propylamine is electronegative, enabling it to attract hydrogen atoms from other propylamine molecules. This hydrogen bonding affects propylamine's physical properties, such as boiling point and solubility, similar to ethanol.
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Related Practice
Textbook Question

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.

g. HCN

h. CH3CHO

i. H2C=NH

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Textbook Question

Two isomers of 1,2-dichloroethene are known. One has a dipole moment of 2.4 D; the other has zero dipole moment. Draw the two isomers, and explain why one has zero dipole moment.

CHCl=CHCl 1,2-dichloroethene

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1
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Textbook Question

For each pair of compounds, circle the compound you expect to have the higher boiling point. Explain your reasoning.

(d) HOCH2—(CH2)4—CH2OH or (CH3)3CCH(OH)CH3

(e) (CH3CH2CH2)2NH or (CH3CH2)3N

(f)

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Textbook Question

Draw the hydrogen bonding that takes place between

c. a molecule of dimethyl ether and two molecules of water.

d. two molecules of trimethylamine and a molecule of water.

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Textbook Question

For each pair of compounds, circle the compound you expect to have the higher boiling point. Explain your reasoning.

a. (CH3)3C—C(CH3)3 or (CH3)2CH—CH2CH2—CH(CH3)2

b. CH3(CH2)6CH3 or CH3(CH2)5CH2OH

c. CH3CH2OCH2CH3 or CH3CH2CH2CH2OH

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2
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Textbook Question

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.

d. CH3F

e. CF4

f. CH3OH

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