Textbook Question
Which of the following alkenes would you expect to react fastest with HBr in each pair?
(b)
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Ch. 8 - Alkenes I: Properties and Electrophilic Additions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 7, Problem 64
Which of the following cycloalkanes would you expect to produce the least heat upon combustion when measured per CH2? Explain your answer.
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Understand the concept: The heat of combustion is a measure of the energy released when a compound is burned completely in oxygen. For cycloalkanes, the amount of heat released is influenced by the ring strain. Cycloalkanes with less ring strain are more stable and release less heat upon combustion.
Recall the relationship between ring strain and stability: Smaller rings (e.g., cyclopropane and cyclobutane) have higher ring strain due to angle strain and torsional strain. Larger rings (e.g., cyclohexane) tend to have less ring strain because they can adopt conformations that minimize these strains.
Compare the cycloalkanes: Evaluate the ring strain for each cycloalkane in the list. Cyclohexane, for example, adopts a chair conformation that minimizes strain, making it more stable. Cyclopropane and cyclobutane, on the other hand, have significant angle strain and torsional strain, making them less stable.
Relate stability to heat of combustion: The more stable the cycloalkane, the less energy is released during combustion. Therefore, the cycloalkane with the least ring strain will produce the least heat upon combustion.
Conclude based on the analysis: Identify the cycloalkane with the least ring strain (likely cyclohexane) and explain why it produces the least heat upon combustion compared to the others in the list.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Cycloalkanes
Cycloalkanes are saturated hydrocarbons that contain carbon atoms arranged in a ring structure. They are characterized by the general formula CnH2n, where 'n' is the number of carbon atoms. The stability and reactivity of cycloalkanes can vary based on their size and the presence of substituents, which influences their combustion properties.
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Combustion Reaction
A combustion reaction is a chemical process in which a substance reacts rapidly with oxygen, producing heat and light. In organic chemistry, the combustion of hydrocarbons typically results in carbon dioxide and water as products. The amount of heat released during combustion, known as the heat of combustion, depends on the structure of the molecule and the number of carbon and hydrogen atoms present.
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Heat of Combustion
The heat of combustion is the energy released when a substance undergoes complete combustion with oxygen. It is usually expressed in kilojoules per mole (kJ/mol). For cycloalkanes, the heat of combustion can vary based on factors such as ring strain and molecular stability; cycloalkanes with more strain or fewer hydrogen atoms typically release less heat upon combustion.
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Related Practice
Textbook Question
How many stereoisomers are possible for the following alkenes?
(b)
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Textbook Question
Cyclooctene is one of the smaller rings that can form a trans alkene. Would you expect cis-cyclooctene or trans-cyclooctene to react more quickly in an acid-catalyzed hydration reaction?
Textbook Question
Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iii) HBr, H2O2
(k)
Textbook Question
How many stereoisomers are possible for the following alkenes?
(c)
Textbook Question
Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions:(ii) HCl
(k)
3
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