Textbook Question
For each of the following, give the systematic name and the common name (if it has one) and then indicate whether it is a primary, secondary, or tertiary amine:
d.
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Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure
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. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 31a
Bruice 8th EditionCh. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and StructureProblem 31aChapter 4, Problem 31a
Predict the approximate size of the following bond angles.
(a) the C—O—C bond angle in an ether
Verified step by step guidance1
Review the molecular geometry of the ether functional group. In an ether, the central oxygen atom is bonded to two carbon atoms and has two lone pairs of electrons. This gives the oxygen atom a total of four regions of electron density.
Apply the Valence Shell Electron Pair Repulsion (VSEPR) theory. According to VSEPR, the regions of electron density around the oxygen atom will arrange themselves to minimize repulsion. This typically results in a tetrahedral electron geometry.
Understand the impact of lone pairs. Lone pairs of electrons exert greater repulsion than bonding pairs, which slightly compresses the bond angles from the ideal tetrahedral angle of 109.5°.
Estimate the bond angle. Due to the presence of two lone pairs on the oxygen atom, the C—O—C bond angle in an ether is slightly less than 109.5°, typically around 105° to 107°.
Conclude that the approximate bond angle can be predicted based on the tetrahedral geometry and the influence of lone pair repulsion, leading to a slightly reduced angle compared to the ideal tetrahedral value.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Bond Angles
Bond angles are the angles formed between two adjacent bonds at a central atom. They are influenced by the hybridization of the atom and the presence of lone pairs, which can repel bonding pairs and alter the expected angles. Understanding typical bond angles helps predict molecular geometry and reactivity.
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02:46
What is angle strain?
Hybridization
Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate bonding. In ethers, the carbon atoms are typically sp3 hybridized, leading to a tetrahedral arrangement around each carbon. This hybridization affects the bond angles, which are generally around 109.5 degrees in a tetrahedral geometry.
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10:43Using bond sites to predict hybridization
Molecular Geometry
Molecular geometry refers to the three-dimensional arrangement of atoms in a molecule. In the case of ethers, the C—O—C bond angle is influenced by the tetrahedral geometry of the surrounding carbon atoms and the lone pairs on the oxygen atom. This geometry helps predict the physical and chemical properties of the molecule.
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07:44Molecular Geometry Explained.
Related Practice
Textbook Question
Predict the approximate size of the following bond angles.
(b) the C—N—C bond angle in a secondary amine
1
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Textbook Question
For each of the following, give the systematic name and the common name (if it has one) and then indicate whether it is a primary, secondary, or tertiary amine:
b.
7
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Textbook Question
For each of the following, give the systematic name and the common name (if it has one) and then indicate whether it is a primary, secondary, or tertiary amine:
c.
1
views
Textbook Question
What is the smallest straight-chain alkane that is a liquid at room temperature (which is about 25 °C)?
1
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Textbook Question
Predict the approximate size of the following bond angles.
(d) the C—N—C bond angle in a quaternary ammonium salt
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