Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D2, Pd/C.
(h)
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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 45h(viii)
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (viii) 1. O3 2. CH3SCH3
(h) 
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 of 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 structure. The double bond will be the site of cleavage during the reaction.
Step 3: Break the double bond. Conceptually split the double bond into two parts, and attach an oxygen atom to each carbon that was originally part of the double bond. This forms two carbonyl groups.
Step 4: Determine the type of carbonyl compounds formed. If the carbon attached to the double bond has one hydrogen, the product will be an aldehyde. If it has no hydrogens, the product will be a ketone. Use this rule to assign the correct carbonyl products.
Step 5: Confirm the reductive workup. The use of CH₃SCH₃ ensures that the products remain aldehydes or ketones, as it prevents further oxidation to carboxylic acids. Write the final products based on the cleavage and the reductive workup conditions.
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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), resulting in the formation of carbonyl compounds such as aldehydes or ketones. The reaction typically proceeds through the formation of a cyclic ozonide intermediate, which is then reduced to yield the final products. Understanding this process is crucial for predicting the products of the reaction in the given question.
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General properties of ozonolysis.
Thioether Reduction
In the context of the reaction, 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. Recognizing the role of thioethers in this reduction process is essential for determining the final products of the reaction.
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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 position of the double bond in the alkene influences the location of the carbonyl groups formed. Understanding regioselectivity helps in predicting which products will be favored in the reaction under the specified conditions.
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Related Practice
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ii) Cl2
(h)
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br2
(h)
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl2, CH3OH
(k)
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H2, Pd/C;
(h)
1
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Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br2, H2O
(k)
4
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