Textbook Question
For each pair of structures, determine whether they represent different compounds or a single compound.
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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 17a
Predict the hybridization, geometry, and bond angles for the central atoms in
a. but-2-ene, CH3CH=CHCH3
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Identify the central atoms in but-2-ene. The central atoms are the two carbon atoms involved in the double bond, which are the second and third carbon atoms in the chain.
Determine the hybridization of the central carbon atoms. In but-2-ene, the carbon atoms involved in the double bond are sp² hybridized. This is because each carbon forms three sigma bonds and has one pi bond.
Predict the geometry around the sp² hybridized carbon atoms. The geometry is trigonal planar, which is typical for sp² hybridized atoms.
Estimate the bond angles around the sp² hybridized carbon atoms. In a trigonal planar geometry, the bond angles are approximately 120 degrees.
Consider the overall structure of but-2-ene. The molecule is planar around the double bond, and the geometry and bond angles are consistent with the sp² hybridization of the central carbon atoms.
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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 process of mixing atomic orbitals to form new hybrid orbitals, which can form sigma bonds or accommodate lone pairs. In but-2-ene, the central carbon atoms involved in the double bond are sp2 hybridized, meaning one s orbital and two p orbitals combine to form three equivalent sp2 orbitals, allowing for a planar structure with 120-degree bond angles.
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Molecular Geometry
Molecular geometry refers to the three-dimensional arrangement of atoms around a central atom. For sp2 hybridized atoms, as in the case of the central carbons in but-2-ene, the geometry is trigonal planar. This means the atoms bonded to the central carbon lie in a single plane, forming a triangular shape with 120-degree angles between them.
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Bond Angles
Bond angles are the angles between adjacent bonds at an atom. In but-2-ene, the sp2 hybridization of the central carbon atoms results in bond angles of approximately 120 degrees. This is characteristic of a trigonal planar geometry, where the electron pairs are evenly distributed around the central atom to minimize repulsion, according to VSEPR theory.
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Related Practice
Textbook Question
Predict the hybridization, geometry, and bond angles for the carbon and nitrogen atoms in acetonitrile (CH3–C≡N:).
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Textbook Question
Predict the hybridization, geometry, and bond angles for the central atoms in
b. CH3CH=NH
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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.
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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.
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Textbook Question
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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