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 18
Predict the hybridization, geometry, and bond angles for the carbon and nitrogen atoms in acetonitrile (CH3–C≡N:).
Verified step by step guidance1
Identify the structure of acetonitrile, which is CH3C≡N. The molecule consists of a methyl group (CH3) attached to a carbon-nitrogen triple bond.
Determine the hybridization of the carbon atom in the methyl group (CH3). The carbon is bonded to three hydrogen atoms and one other carbon atom, making a total of four sigma bonds. This suggests sp3 hybridization.
Determine the geometry around the sp3 hybridized carbon atom in the methyl group. With sp3 hybridization, the geometry is tetrahedral, and the bond angles are approximately 109.5 degrees.
Examine the carbon atom in the carbon-nitrogen triple bond (C≡N). This carbon is involved in one sigma bond with the nitrogen and one sigma bond with the adjacent carbon, along with two pi bonds. This indicates sp hybridization.
Determine the geometry around the sp hybridized carbon and nitrogen atoms in the C≡N group. The geometry is linear, with bond angles of 180 degrees, due to the sp hybridization.
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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 acetonitrile, the carbon atom bonded to nitrogen is sp hybridized, resulting in a linear geometry, while the carbon in the methyl group is sp3 hybridized, leading to a tetrahedral geometry.
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Using bond sites to predict hybridization
Molecular Geometry
Molecular geometry refers to the three-dimensional arrangement of atoms in a molecule. For acetonitrile, the carbon-nitrogen triple bond results in a linear geometry around the sp hybridized carbon and nitrogen atoms, while the sp3 hybridized carbon in the methyl group has a tetrahedral geometry.
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Bond Angles
Bond angles are the angles between adjacent bonds in a molecule. In acetonitrile, the sp hybridized carbon and nitrogen atoms form a linear structure with a bond angle of 180 degrees. The sp3 hybridized carbon in the methyl group has bond angles of approximately 109.5 degrees, typical for a tetrahedral 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
Which of the following compounds show cis-trans isomerism? Draw the cis and trans isomers of those that do.
(a) CHF=CHF
(b) F2C=CH2
(c) CH2=CH–CH2–CH3
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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
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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