Textbook Question
Why does cis-2-butene have a higher boiling point than trans-2-butene?
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Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis
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. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 8a,b,c
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 8a,b,cChapter 8, Problem 8a,b,c
What orbitals are used to form the carbon–carbon s bond between the highlighted carbons?
a. 
b. 
c. 
Verified step by step guidance1
Identify the highlighted carbons in the structure. In the first image, the highlighted carbons are part of a single bond (σ bond) between two sp3 hybridized carbons. In the second image, the highlighted carbons are part of a double bond (σ and π bonds) between an sp2 hybridized carbon and an sp3 hybridized carbon. In the third image, the highlighted carbons are part of a triple bond (σ and two π bonds) between two sp hybridized carbons.
Understand the hybridization of the carbons involved. Hybridization determines the type of orbitals used in bonding. For sp3 hybridized carbons, the σ bond is formed using sp3 orbitals. For sp2 hybridized carbons, the σ bond is formed using sp2 orbitals, and the π bond is formed using unhybridized p orbitals. For sp hybridized carbons, the σ bond is formed using sp orbitals, and the π bonds are formed using unhybridized p orbitals.
Analyze the bonding in the first image. The carbon-carbon σ bond is formed by the overlap of two sp3 orbitals, as both carbons are sp3 hybridized.
Analyze the bonding in the second image. The carbon-carbon σ bond is formed by the overlap of an sp2 orbital from one carbon and an sp3 orbital from the other carbon. The π bond is formed by the side-by-side overlap of unhybridized p orbitals from the sp2 hybridized carbon.
Analyze the bonding in the third image. The carbon-carbon σ bond is formed by the overlap of two sp orbitals, and the two π bonds are formed by the side-by-side overlap of unhybridized p orbitals from each sp hybridized carbon.
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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 by which atomic orbitals mix to form new hybrid orbitals that are suitable for the pairing of electrons to form chemical bonds. In carbon, the most common hybridizations are sp3, sp2, and sp, which correspond to different types of bonding and molecular geometries. Understanding hybridization is crucial for determining the types of bonds formed between carbon atoms.
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Sigma Bonds
A sigma (σ) bond is a type of covalent bond formed by the head-on overlap of atomic orbitals. In the case of carbon–carbon bonds, the overlap can occur between hybrid orbitals (like sp3 or sp2) or between an s orbital and a hybrid orbital. Sigma bonds are characterized by their cylindrical symmetry around the bond axis and are the first bonds formed between two atoms.
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Orbital Overlap
Orbital overlap refers to the extent to which atomic orbitals from two atoms share the same space when forming a bond. The greater the overlap, the stronger the bond. In carbon–carbon bonds, understanding how the specific orbitals overlap (such as s, p, or hybrid orbitals) is essential for predicting bond strength and molecular structure.
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Related Practice
Textbook Question
Name the following:
b.
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Textbook Question
What orbitals are used to form the carbon–carbon s bond between the highlighted carbons?
g.
h.
i.
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Textbook Question
Name the following:
a.
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Textbook Question
Draw the structures and give the common and systematic names for the seven alkynes with molecular formula C6H10.
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Textbook Question
In Table 7.2, what is the smallest alkane, the smallest terminal alkene, and the smallest terminal alkyne that are liquids at room temperature, which is generally taken to be 20 °C to 25 °C?
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