Textbook Question
Predict the hybridization, geometry, and bond angles for the central atoms in
a. but-2-ene, CH3CH=CHCH3
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Ch.1 - Structure and Bonding
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 1, Problem 16a
Predict the hybridization of the oxygen atom in water, H2O. Draw a picture of its three-dimensional structure, and explain why its bond angle is 104.5°.
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Identify the central atom in the molecule. In water (H2O), the central atom is oxygen.
Determine the number of valence electrons for the oxygen atom. Oxygen has 6 valence electrons.
Consider the bonding and lone pairs around the oxygen atom. In H2O, oxygen forms two sigma bonds with hydrogen atoms and has two lone pairs of electrons.
Use the VSEPR (Valence Shell Electron Pair Repulsion) theory to predict the hybridization. The steric number (number of sigma bonds + lone pairs) for oxygen in H2O is 4, indicating sp³ hybridization.
Explain the bond angle. The ideal bond angle for sp³ hybridization is 109.5°, but the presence of lone pairs, which exert greater repulsion than bonding pairs, reduces the bond angle to approximately 104.5°.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Hybridization
Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals suitable for pairing electrons to form chemical bonds. In water (H2O), the oxygen atom undergoes sp3 hybridization, which involves the mixing of one s orbital and three p orbitals, resulting in four equivalent sp3 hybrid orbitals. This hybridization explains the tetrahedral arrangement of electron pairs around the oxygen atom.
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Using bond sites to predict hybridization
Molecular Geometry
Molecular geometry refers to the three-dimensional arrangement of atoms within a molecule. In water, the geometry is bent or V-shaped due to the two lone pairs on the oxygen atom, which repel the hydrogen atoms, resulting in a bond angle of 104.5°. This angle is less than the ideal tetrahedral angle of 109.5° due to the greater repulsion exerted by lone pairs compared to bonding pairs.
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VSEPR Theory
Valence Shell Electron Pair Repulsion (VSEPR) theory is used to predict the shape of molecules based on electron pair repulsions. According to VSEPR theory, electron pairs around a central atom will arrange themselves to minimize repulsion. In H2O, the two lone pairs on oxygen push the hydrogen atoms closer together, resulting in a bond angle of 104.5°, which is characteristic of a bent molecular shape.
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Related Practice
Textbook Question
Compute the empirical and molecular formulas for each of the following elemental analyses. In each case, propose at least one structure that fits the molecular formula.
3
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Textbook Question
Predict the hybridization, geometry, and bond angles for the central atoms in
b. CH3CH=NH
1
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Textbook Question
The electrostatic potential maps for ammonia and water are shown here. The structure of ammonia is shown within its EPM. Note how the lone pair creates a region of high electron potential (red), and the hydrogens are in regions of low electron potential (blue). Show how your three-dimensional structure of water corresponds with its EPM.
1
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Textbook Question
Compute the empirical and molecular formulas for each of the following elemental analyses. In each case, propose at least one structure that fits the molecular formula.
3
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Textbook Question
Make a model of propane (C3H8), and draw this model using dashed lines and wedges to represent bonds going back and coming forward.
2
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