Textbook Question
The following ethers are ranked according to their ability to form explosive peroxides. Explain this ranking based on your knowledge of the reaction mechanism.
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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 56
Mullins 1st EditionCh. 11 - Properties and Synthesis of Alkyl Halides: Radical ReactionsProblem 56Chapter 10, Problem 56
If a small amount of a moderately nonpolar poisonous compound was added to a pond, why would it be safer to drink the water than it would be to eat the fish that live there?
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Understand the concept of bioaccumulation: Bioaccumulation refers to the process by which organisms accumulate toxic substances, such as nonpolar compounds, at a rate faster than they can eliminate them.
Consider the solubility of nonpolar compounds: Nonpolar compounds tend to be more soluble in organic solvents and lipids than in water. This means they are more likely to accumulate in the fatty tissues of organisms, such as fish, rather than remaining dissolved in the water.
Analyze the food chain dynamics: Fish, being higher up in the food chain, can accumulate higher concentrations of the nonpolar compound through their diet, as they consume smaller organisms that have absorbed the compound.
Evaluate the concentration effect: The concentration of the nonpolar compound in the fish is likely to be higher than in the water due to bioaccumulation, making the fish more hazardous to consume.
Conclude with risk assessment: Drinking the water, which contains a lower concentration of the compound, poses less risk than eating the fish, which have accumulated higher levels of the toxin in their tissues.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Polarity and Solubility
Polarity refers to the distribution of electrical charge over the atoms in a molecule. Nonpolar compounds tend to be hydrophobic, meaning they do not dissolve well in water. This concept is crucial because it explains why the nonpolar compound might not mix thoroughly with the pond water, making the water safer to drink than consuming fish that may accumulate the compound.
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Functional Classification
Bioaccumulation
Bioaccumulation is the process by which organisms accumulate substances, such as pesticides or other chemicals, in their bodies over time. Fish can absorb nonpolar compounds from the water and store them in their fatty tissues, leading to higher concentrations than in the surrounding water. Understanding this concept helps explain why eating fish could be more dangerous than drinking the water.
Food Chain and Biomagnification
Biomagnification refers to the increase in concentration of a substance in a food chain. As small fish consume contaminated water and are eaten by larger fish, the concentration of the nonpolar compound increases at each trophic level. This concept is essential for understanding why the compound's concentration might be higher in fish than in the water, posing a greater risk when consuming fish.
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Related Practice
Textbook Question
Tributyltin hydride (Bu3SnH) is often used as a 'radical carrier' in radical reactions. Which bond would you expect to be weaker, Sn–H or C–H? How might this relate to radical stability? Explain your answer.
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Textbook Question
Haloalkanes can be reduced to alkanes using radical reactions involving Bu₃SnH and a catalytic amount of AIBN. Suggest a mechanism for this reaction. [Pay close attention to the bonds formed and broken in developing your mechanism.]
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Textbook Question
The solvent tetrahydrofuran (THF) is often sold with a small amount of BHT added. Provide a mechanism that explains why this might be so.
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Textbook Question
Other molecules can be used as initiators in radical reactions. One such molecule is 2, 2'-azobisisobutyronitrile (AIBN). Show an arrow-pushing mechanism that rationalizes the formation of the following radical species. What are the driving forces of this reaction?
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Textbook Question
One danger associated with storing ether solvents is their tendency to form explosive peroxides when exposed to oxygen. Suggest a mechanism by which the hydroperoxide might form. You can assume the presence of X• to start the reaction.
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