Textbook Question
Draw the structure that corresponds to the compound names shown.
(a) (S)-3-bromo-3-ethylcyclohex-1-ene
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Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions
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
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Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblem 35
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblem 35Chapter 10, Problem 35
The following polyunsaturated fat, which does not exist in nature, is oxidized at a rate similar to oleic acid (Table 11.14), despite having two cis-alkenes. Why?
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Examine the structure of the polyunsaturated fat provided in the image. It contains two cis-alkene groups, which are double bonds with both hydrogen atoms on the same side of the double bond.
Understand that the oxidation rate of fatty acids is influenced by the presence and position of double bonds. Cis-alkenes can affect the molecular geometry and packing of the fatty acid chains.
Consider the role of double bonds in the oxidation process. Double bonds are sites of reactivity, and their presence can increase the susceptibility of the molecule to oxidation.
Compare the structure to oleic acid, which is a monounsaturated fatty acid with one cis double bond. Despite having two cis-alkenes, the polyunsaturated fat may have a similar oxidation rate due to similar structural features that affect reactivity.
Recognize that the overall molecular structure, including the length of the carbon chain and the position of double bonds, can lead to similar oxidation rates between the polyunsaturated fat and oleic acid, despite differences in the number of double bonds.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Polyunsaturated Fats
Polyunsaturated fats contain multiple double bonds in their carbon chain. These double bonds can be in cis or trans configurations, affecting the fat's physical properties and reactivity. The presence of multiple double bonds generally increases susceptibility to oxidation, which is a key factor in determining the stability and shelf life of fats.
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Glycerol Metabolism Concept 1
Oxidation of Fatty Acids
Oxidation of fatty acids involves the reaction of oxygen with the double bonds in the fatty acid structure, leading to the formation of peroxides and other degradation products. The rate of oxidation can be influenced by the number and configuration of double bonds, as well as the presence of antioxidants. Understanding the oxidation process is crucial for evaluating the stability of different fatty acids.
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Cis vs. Trans Configuration
The cis configuration of double bonds in fatty acids results in a bent structure, which affects how closely the molecules can pack together. This packing influences the melting point and physical properties of the fat. In contrast, trans configurations allow for a straighter chain, which can lead to increased stability and a higher melting point, impacting the oxidation rate and overall behavior of the fat.
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Guided course
00:44Is the following cyclohexane cis or trans?
Related Practice
Textbook Question
The fact that allylic halogenation results in formation of the most stable alkene suggests that it is under thermodynamic control. Thus, the second propagation step must be reversible. Suggest an arrow-pushing mechanism by which the less stable allylic halide might equilibrate to the more stable allylic halide.
Textbook Question
Vitamin E, especially the B ring and the side chain, is a terpenoid derivative. Identify the isoprene units nature used to make it.
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Textbook Question
(a) Using bond-dissociation energies (Table 5.6), which of the indicated bonds should break most easily?
(b) How does that help you explain the results shown in Figure 11.40?
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Textbook Question
Predict the products of the following allylic halogenation reactions.
(d)
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Textbook Question
Name the following halogenated compounds according to the IUPAC rules of nomenclature.
(c)
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