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 17b
Predict the hybridization, geometry, and bond angles for the central atoms in
b. CH3CH=NH
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Identify the central atoms in the molecule CH3CH=NH. The central atoms are the carbon in CH3, the carbon in CH=, and the nitrogen in NH.
Determine the hybridization of the carbon in CH3. This carbon is bonded to three hydrogen atoms and one other carbon atom, making a total of four sigma bonds. The hybridization is sp3.
Determine the geometry and bond angles for the sp3 hybridized carbon in CH3. The geometry is tetrahedral, and the bond angles are approximately 109.5 degrees.
Determine the hybridization of the carbon in CH=. This carbon is bonded to one hydrogen atom, one nitrogen atom, and one other carbon atom, with a double bond present. The hybridization is sp2.
Determine the geometry and bond angles for the sp2 hybridized carbon in CH=. The geometry is trigonal planar, and the bond angles are approximately 120 degrees.
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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 the pairing of electrons to form chemical bonds. In CH3CH=NH, the central carbon atom is sp3 hybridized due to its four sigma bonds, while the nitrogen atom is sp2 hybridized because it forms a double bond with carbon and has a lone pair.
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Molecular Geometry
Molecular geometry refers to the three-dimensional arrangement of atoms in a molecule. For CH3CH=NH, the geometry around the sp3 hybridized carbon is tetrahedral, while the geometry around the sp2 hybridized nitrogen is trigonal planar, influenced by the double bond and lone pair.
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Bond Angles
Bond angles are the angles between adjacent bonds in a molecule, determined by the hybridization and geometry. In CH3CH=NH, the sp3 hybridized carbon has bond angles of approximately 109.5°, typical of tetrahedral geometry, while the sp2 hybridized nitrogen has bond angles of about 120°, characteristic of trigonal planar geometry.
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Related Practice
Textbook Question
Predict the hybridization, geometry, and bond angles for the central atoms in
a. but-2-ene, CH3CH=CHCH3
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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
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
Two compounds with the formula CH3–CH=N–CH3 are known.
b. What two compounds have this formula?
c. Explain why only one compound with the formula (CH3)2CNCH3 is known.
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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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