Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br2
(k)
3
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Ch. 9 - Alkenes II: Oxidation and Reduction
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 8, Problem 45k(viii)
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (viii) 1. O3 2. CH3SCH3
(k) 
Verified step by step guidance1
Step 1: Recognize the reaction type. The reaction involves ozonolysis of an alkene, which is a process where the double bond in the alkene is cleaved by ozone (O₃) to form carbonyl compounds (aldehydes or ketones). The second step, using dimethyl sulfide (CH₃SCH₃), is a reductive workup that prevents the formation of carboxylic acids.
Step 2: Identify the structure of the alkene. Determine the position of the double bond in the given alkene. The double bond will be the site of cleavage during the reaction.
Step 3: Break the double bond symmetrically. Using the structure of the alkene, split the double bond into two parts. Each carbon atom of the double bond will form a bond with an oxygen atom from ozone, resulting in an intermediate ozonide.
Step 4: Apply the reductive workup. The ozonide intermediate is then treated with dimethyl sulfide (CH₃SCH₃), which reduces the ozonide to carbonyl compounds. Each carbon atom originally part of the double bond will become part of a carbonyl group (C=O).
Step 5: Determine the final products. Based on the structure of the original alkene, identify the specific carbonyl compounds (aldehydes or ketones) formed. If the double bond is internal, ketones are typically formed. If the double bond is terminal, aldehydes are formed.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ozonolysis
Ozonolysis is a reaction involving the cleavage of alkenes using ozone (O₃) to form carbonyl compounds. The process typically occurs in two steps: first, the alkene reacts with ozone to form a molozonide, which rearranges to form ozonide. This ozonide can then be reduced to yield aldehydes or ketones, depending on the structure of the original alkene.
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General properties of ozonolysis.
Thioether Reduction
In the context of organic reactions, thioethers like dimethyl sulfide (CH₃SCH₃) can act as reducing agents. After ozonolysis, the carbonyl compounds formed can be further reduced by thioethers, leading to the formation of alcohols or other reduced products. This step is crucial for understanding the final products of the reaction sequence.
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Regioselectivity
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In ozonolysis, the regioselectivity of the reaction can influence the types of carbonyl products formed, which is important when predicting the final products after the reduction step with dimethyl sulfide.
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Related Practice
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1
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