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Ch. 2 - Acids and Bases; Functional Groups
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Tutti i libri di testoWade 9th EditionCh. 2 - Acids and Bases; Functional GroupsProblema 31a-d
Capitolo 2, Problema 31a-d

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

Guida verificata passo dopo passo
1
Step 1: Understand the concept of hydrogen bonding. Hydrogen bonds occur when hydrogen is covalently bonded to a highly electronegative atom like nitrogen, oxygen, or fluorine, allowing for interaction with lone pairs on these atoms in other molecules.
Step 2: Analyze each compound to determine if it can form hydrogen bonds. Look for the presence of N-H or O-H bonds, as these are indicative of hydrogen bonding capability.
Step 3: For compound (a) \((CH_3CH_2)_2NH\), identify the N-H bond. This bond allows the compound to form hydrogen bonds both internally and with water, due to the lone pairs on nitrogen.
Step 4: For compound (b) \((CH_3CH_2)_3N\), note the absence of N-H bonds. This compound cannot form hydrogen bonds internally but can interact with water through lone pairs on nitrogen, though less effectively.
Step 5: For compounds (c) \(CH_3CH_2CH_2OH\) and (d) \((CH_3CH_2CH_2)_2OH\), identify the O-H bonds. These compounds can form hydrogen bonds both internally and with water, enhancing their solubility in water due to the polar nature of the O-H group.

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Hydrogen Bonding

Hydrogen bonding occurs when a hydrogen atom is covalently bonded to a highly electronegative atom, such as nitrogen, oxygen, or fluorine, allowing it to interact with lone pairs on other electronegative atoms. This interaction is crucial for determining the solubility and boiling points of compounds.
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The definition of hydrogenation.

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 or -NH are more likely to dissolve in water due to their ability to interact with water's polar nature, enhancing solubility.
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Percorso guidato
1:35
Metal Ion Catalysis: Water Activation Concept 1

Functional Groups

Functional groups such as alcohols (-OH) and amines (-NH) are key in determining a compound's chemical behavior, including hydrogen bonding and solubility. Alcohols can form hydrogen bonds due to the presence of an -OH group, while amines can do so with an -NH group, affecting their interaction with water.
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Identifying Functional Groups
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Domanda del libro di testo

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.

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

(c)

(d)

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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

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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.

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Domanda del libro di testo

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.

d.

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Domanda del libro di testo

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

(a)

(b)

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