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 8g,h,i
Bruice 8th EditionCh. 7 - The Reactions of Alkynes • An Introduction to Multistep SynthesisProblem 8g,h,iChapter 8, Problem 8g,h,i
What orbitals are used to form the carbon–carbon s bond between the highlighted carbons?
g. 
h. 
i. 
Verified step by step guidance1
Step 1: Analyze the bonding in each structure. In organic molecules, sigma (σ) bonds are formed by the overlap of orbitals. The type of orbitals involved depends on the hybridization of the atoms forming the bond.
Step 2: For structure (i), the highlighted carbons are part of a double bond. Double bonds consist of one sigma bond and one pi bond. The sigma bond is formed by the overlap of sp² hybrid orbitals from each carbon atom.
Step 3: For structure (ii), the highlighted carbons are part of a triple bond. Triple bonds consist of one sigma bond and two pi bonds. The sigma bond is formed by the overlap of sp hybrid orbitals from each carbon atom.
Step 4: For structure (iii), the highlighted carbons are part of a double bond. Similar to structure (i), the sigma bond is formed by the overlap of sp² hybrid orbitals from each carbon atom.
Step 5: Summarize the orbital interactions: (i) sp²-sp² overlap for the sigma bond, (ii) sp-sp overlap for the sigma bond, and (iii) sp²-sp² overlap for the sigma bond.
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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 bonding. In carbon, the most common hybridizations are sp3, sp2, and sp, which correspond to single, double, and triple bonds, respectively. Understanding hybridization is crucial for predicting the geometry and bond angles in molecules.
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Using bond sites to predict hybridization
Sigma (σ) Bonds
Sigma bonds are the first bonds formed between two atoms and are characterized by the head-on overlap of orbitals. In carbon–carbon bonds, σ bonds can be formed by the overlap of sp3, sp2, or sp hybrid orbitals. Recognizing the type of σ bond is essential for understanding molecular structure and reactivity.
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Bonding Orbitals
Bonding orbitals are regions in a molecule where the probability of finding electrons is high, leading to the formation of chemical bonds. In the context of carbon–carbon bonds, the specific orbitals involved (such as sp3, sp2, or sp) determine the bond's strength and characteristics. Identifying these orbitals is key to analyzing molecular interactions.
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Related Practice
Textbook Question
Name the following:
b.
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Textbook Question
Drawing on what you know about the stereochemistry of alkene addition reactions,
a. write the mechanism for the reaction of 2-butyne with one equivalent of Br2.
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Textbook Question
Name the following:
a.
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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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Textbook Question
What orbitals are used to form the carbon–carbon s bond between the highlighted carbons?
a.
b.
c.
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