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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 5c,d
Capitolo 2, Problema 5c,d

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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Step 1: Understand the concept of hydrogen bonding. Hydrogen bonds are a type of dipole-dipole interaction that occurs between a hydrogen atom bonded to a highly electronegative atom (such as oxygen, nitrogen, or fluorine) and another electronegative atom with a lone pair of electrons.
Step 2: For part c, identify the functional groups involved. Dimethyl ether has an oxygen atom with lone pairs, and water molecules have oxygen atoms with lone pairs and hydrogen atoms that can participate in hydrogen bonding.
Step 3: Draw the structure of dimethyl ether, which is \( \text{CH}_3\text{OCH}_3 \), and two water molecules \( \text{H}_2\text{O} \). Show the lone pairs on the oxygen atoms in both dimethyl ether and water molecules.
Step 4: Illustrate the hydrogen bonds. The oxygen atom in dimethyl ether can form hydrogen bonds with the hydrogen atoms of the water molecules. Draw dashed lines to represent these hydrogen bonds between the oxygen of dimethyl ether and the hydrogen atoms of water.
Step 5: For part d, identify the functional groups involved. Trimethylamine has a nitrogen atom with a lone pair, and water has oxygen atoms with lone pairs and hydrogen atoms. Draw the structure of trimethylamine \( \text{(CH}_3\text{)}_3\text{N} \) and a water molecule \( \text{H}_2\text{O} \). Show the hydrogen bonds between the nitrogen atom of trimethylamine and the hydrogen atoms of the water molecule.

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Hydrogen Bonding

Hydrogen bonding is a type of dipole-dipole interaction that occurs when a hydrogen atom, covalently bonded to a highly electronegative atom like 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 structure and properties of compounds.
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The definition of hydrogenation.

Electronegativity

Electronegativity refers to the ability of an atom to attract shared electrons in a chemical bond. In the context of hydrogen bonding, atoms like oxygen and nitrogen have high electronegativity, which allows them to attract hydrogen atoms from nearby molecules, facilitating the formation of hydrogen bonds. Understanding electronegativity is essential for predicting molecular interactions.
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Electronegativity

Molecular Structure and Polarity

The molecular structure and polarity of a compound determine its ability to form hydrogen bonds. Dimethyl ether has a polar C-O bond, allowing it to interact with water molecules, while trimethylamine has a lone pair on nitrogen, enabling hydrogen bonding with water. Recognizing these structural features helps in visualizing and drawing hydrogen bonding interactions.
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Molecular Polarity
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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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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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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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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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Draw the hydrogen bonding that takes place between

a. two molecules of ethanol.

b. two molecules of propylamine.

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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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