Textbook Question
Describe the orbitals used in bonding and the bond angles in the following compounds:
d. N2
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Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)Problem 45c,d
Bruice 8th EditionCh. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)Problem 45c,dChapter 2, Problem 45c,d
Predict the approximate bond angles for
c. the H—C—N bond angle in (CH3)2NH.
d. the H—C—O bond angle in CH3OCH3
Verified step by step guidance1
Step 1: Understand the molecular geometry of the compounds. For (CH3)2NH, the nitrogen atom is sp3 hybridized, and the molecule has a trigonal pyramidal geometry due to the lone pair on nitrogen. For CH3OCH3, the oxygen atom is sp3 hybridized, and the molecule has a bent geometry due to the two lone pairs on oxygen.
Step 2: Recall the ideal bond angles for sp3 hybridized atoms. In a perfect tetrahedral geometry, the bond angles are approximately 109.5°. However, lone pairs exert greater repulsion than bonding pairs, which reduces the bond angles slightly.
Step 3: For (CH3)2NH, the lone pair on nitrogen causes the H—C—N bond angle to be slightly less than 109.5°. The repulsion from the lone pair compresses the bond angle, making it closer to approximately 107°.
Step 4: For CH3OCH3, the two lone pairs on oxygen exert repulsion on the bonding pairs, reducing the H—C—O bond angle. This bond angle is slightly less than 109.5°, typically around 104.5°.
Step 5: Summarize the reasoning: The bond angles are influenced by the hybridization of the central atom and the repulsion caused by lone pairs. Lone pairs reduce bond angles compared to the ideal tetrahedral angle of 109.5°.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
VSEPR Theory
Valence Shell Electron Pair Repulsion (VSEPR) Theory is a model used to predict the geometry of individual molecules based on the repulsion between electron pairs in the valence shell of the central atom. According to VSEPR, electron pairs will arrange themselves to minimize repulsion, leading to specific bond angles characteristic of different molecular shapes.
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Equipment and Theory
Hybridization
Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate bonding. In organic molecules, carbon typically undergoes sp3 hybridization, resulting in tetrahedral geometry with bond angles of approximately 109.5 degrees, while nitrogen can exhibit sp3 hybridization as well, influencing the bond angles in amines like (CH3)2NH.
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Molecular Geometry
Molecular geometry refers to the three-dimensional arrangement of atoms within a molecule. The geometry is determined by the number of bonding pairs and lone pairs of electrons around the central atom, which directly influences bond angles. For example, in CH3OCH3, the presence of lone pairs on oxygen affects the H—C—O bond angle, leading to deviations from the ideal tetrahedral angle.
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Related Practice
Textbook Question
Which of the following molecules would you expect to have a dipole moment of zero?
a. CH3CH3
b. H2C═O
c. CH2Cl2
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Textbook Question
Describe the orbitals used in bonding and the bond angles in the following compounds:
e. BF3
1123
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Textbook Question
Which of the following molecules would you expect to have a dipole moment of zero?
d. NH3
e. H2C═CH2
f. H2C═CHBr
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Textbook Question
What is the hybridization of each of the C, N, and O atoms in the following compounds:
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Textbook Question
Which of the following molecules would you expect to have a dipole moment of zero?
g. BeCl2
h. BF3
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