Textbook Question
Rank the following compounds from highest dipole moment to lowest dipole moment:
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Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)
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. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)Problem 65d
Bruice 8th EditionCh. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)Problem 65dChapter 2, Problem 65d
For each of the following molecules, indicate the hybridization of each carbon and give the approximate values of all the bond angles:
d. CH2═CH—CH═CH2
Verified step by step guidance1
Step 1: Identify the structure of the molecule CH₂═CH—CH═CH₂. This molecule consists of four carbon atoms connected in a conjugated system with alternating double and single bonds. The structure is linear for the double-bonded carbons and planar for the entire molecule due to conjugation.
Step 2: Determine the hybridization of each carbon atom. For a carbon atom involved in a double bond (C═C), it is sp² hybridized because it forms three sigma bonds (one sigma bond with the other carbon and two sigma bonds with hydrogens or adjacent carbons) and one unhybridized p orbital forms the π bond.
Step 3: Assign the hybridization to each carbon atom in the molecule. The first and last carbons (CH₂ groups) are sp² hybridized because they are part of a double bond. The middle two carbons (CH groups) are also sp² hybridized for the same reason.
Step 4: Determine the bond angles around each carbon atom. For sp² hybridized carbons, the bond angles are approximately 120° because the electron domains are arranged in a trigonal planar geometry to minimize electron repulsion.
Step 5: Summarize the results. All four carbon atoms in CH₂═CH—CH═CH₂ are sp² hybridized, and the bond angles around each carbon are approximately 120°. The molecule is planar due to the conjugated π system.
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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 that can accommodate the bonding requirements of a molecule. In organic chemistry, carbon typically undergoes sp3, sp2, or sp hybridization depending on its bonding. For example, sp2 hybridization involves one s and two p orbitals mixing to form three equivalent sp2 hybrid orbitals, which are arranged in a trigonal planar geometry.
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Bond Angles
Bond angles are the angles formed between adjacent bonds in a molecule, which are influenced by the hybridization of the atoms involved. For sp3 hybridized carbons, the bond angle is approximately 109.5 degrees, while for sp2 hybridized carbons, the bond angle is about 120 degrees. Understanding bond angles helps predict the molecular geometry and reactivity of organic compounds.
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Alkenes and Their Structure
Alkenes are hydrocarbons that contain at least one carbon-carbon double bond, which affects their hybridization and geometry. In the given molecule CH2═CH—CH═CH2, the carbon atoms involved in double bonds are sp2 hybridized, leading to a planar structure around those carbons. This structural characteristic influences the bond angles and overall reactivity of the alkene.
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Related Practice
Textbook Question
For each of the following molecules, indicate the hybridization of each carbon and give the approximate values of all the bond angles:
a. CH3C≡CH
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Textbook Question
In which orbitals are the lone pairs in nicotine?
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Textbook Question
For each of the following molecules, indicate the hybridization of each carbon and give the approximate values of all the bond angles:
b. CH3CH═CH2
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Textbook Question
Draw a Lewis structure for each of the following:
c. (CH3)2CHCH(CH3)CH2C(CH3)3
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Textbook Question
Show the direction of the dipole moment in each of the following bonds (use the electronegativities given in [Table 1.3] ):
a. H3C—Br
b. H3C—Li
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