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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 6d,e,f
Chapter 2, Problem 6d,e,f

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) Two chemical structures are shown: one with an NH group and another with an NH2 group, indicating a comparison of properties.

Verified step by step guidance
1
Step 1: Understand the concept of boiling point. Boiling point is the temperature at which a substance transitions from a liquid to a gas. It is influenced by intermolecular forces such as hydrogen bonding, dipole-dipole interactions, and van der Waals forces.
Step 2: Analyze the molecular structure of each compound. For compound d, HOCH2—(CH2)4—CH2OH is a linear diol, while (CH3)3CCH(OH)CH3 is a branched alcohol. Linear molecules generally have stronger van der Waals forces due to greater surface area, potentially leading to higher boiling points.
Step 3: Consider hydrogen bonding. Both compounds in pair d can form hydrogen bonds due to the presence of hydroxyl groups (-OH). However, the linear diol can form more extensive hydrogen bonding networks compared to the branched alcohol, which may increase its boiling point.
Step 4: Examine the nitrogen-containing compounds in pair e. (CH3CH2CH2)2NH is a secondary amine, while (CH3CH2)3N is a tertiary amine. Secondary amines can form hydrogen bonds, whereas tertiary amines cannot, due to the lack of a hydrogen atom bonded to nitrogen. This suggests that the secondary amine may have a higher boiling point.
Step 5: Analyze the image for pair f. The image shows two cyclic amines: one with an NH group and the other with an NH2 group. The NH2 group can form more hydrogen bonds compared to the NH group, potentially leading to a higher boiling point for the compound with the NH2 group.

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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 strong type of dipole-dipole interaction that occurs when hydrogen is bonded to highly electronegative atoms like oxygen, nitrogen, or fluorine. This interaction significantly increases the boiling point of a compound because more energy is required to break these bonds during the phase transition from liquid to gas. In the context of the question, compounds with more hydrogen bonding sites will generally have higher boiling points.
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Molecular Structure and Surface Area

The molecular structure and surface area of a compound affect its boiling point. Linear or less branched molecules have greater surface area, leading to stronger van der Waals forces, which increase boiling points. In contrast, more compact or branched structures have less surface area, resulting in weaker intermolecular forces and lower boiling points. This concept helps in comparing the boiling points of the given compounds based on their structural differences.
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Functional Groups and Polarity

Functional groups in organic molecules influence their polarity and, consequently, their boiling points. Polar functional groups, such as hydroxyl (OH) and amino (NH2) groups, enhance intermolecular attractions like hydrogen bonding, raising the boiling point. In the given question, the presence and type of functional groups in each compound determine their relative boiling points by affecting the overall polarity and intermolecular interactions.
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Related Practice
Textbook Question

Calculate the pH of the following solutions.

a. 5.00 g of HBr in 100 mL of aqueous solution

b. 1.50 g of NaOH in 50 mL of aqueous solution

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Textbook Question

Ammonia appears in [TABLE 2-2 ] as both an acid and a conjugate base. a. Explain how ammonia can act as both an acid and a base. Which of these roles does it commonly fill in aqueous solutions?

b. Show how water can serve as both an acid and a base.

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Textbook Question

Circle the member of each pair that is more soluble in water.

a. CH3CH2OCH2CH3 or CH3CH2CH2CH2CH3

b. CH3CH2OCH2CH3 or CH3CH2CH2OH

c. CH3CH2NHCH3 or CH3CH2CH2CH3

d. CH3CH2OH or CH3CH2CH2CH2OH

e.

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Textbook Question

Draw the hydrogen bonding that takes place between

a. two molecules of ethanol.

b. two molecules of propylamine.

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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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