Textbook Question
Draw the product(s) you'd expect when each of these alkenes is treated first with O3, then with CH3SCH3
(c)
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 30b
Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene.
(b) 
Verified step by step guidance1
Identify the products of the ozonolysis reaction: acetophenone (C₆H₅C(O)CH₃) and formaldehyde (HCHO).
Recognize that ozonolysis cleaves the double bond of an alkene to form carbonyl compounds. The products suggest the original alkene had a structure that splits into these two fragments.
Determine the structure of the alkene that would yield acetophenone and formaldehyde upon ozonolysis. The alkene must have a double bond between the carbon atoms that will form the carbonyl groups in the products.
Consider the connectivity of the alkene: the carbon atom that forms acetophenone must be connected to the phenyl group and a methyl group, while the carbon atom that forms formaldehyde must be connected to a hydrogen atom.
Propose the structure of the alkene: phenylpropene (C₆H₅CH=CH₂), where the double bond is between the terminal carbon and the adjacent carbon, allowing for the formation of acetophenone and formaldehyde upon ozonolysis.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ozonolysis Reaction
Ozonolysis is a reaction where ozone (O3) cleaves alkenes to form carbonyl compounds, such as aldehydes and ketones. The reaction involves the formation of an ozonide intermediate, which is then reduced to yield the final products. This process is useful for determining the position of double bonds in alkenes and synthesizing specific carbonyl compounds.
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06:30
General properties of ozonolysis.
Alkene Structure
The structure of the alkene is crucial in ozonolysis as it determines the resulting carbonyl compounds. In the given image, the alkene must have a double bond positioned such that upon cleavage, it forms the specified ketone and aldehyde. Understanding the connectivity and substitution pattern of the alkene helps predict the ozonolysis products accurately.
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1:59Alkene Metathesis Concept 5
Reductive Workup
Reductive workup in ozonolysis involves using a reducing agent, such as dimethyl sulfide (CH3SCH3), to convert the ozonide intermediate into stable carbonyl compounds. This step is essential to prevent the formation of unwanted by-products and ensure the desired aldehydes and ketones are obtained. The choice of reducing agent can influence the yield and purity of the final products.
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03:16Reductive Workup Mechanism:
Related Practice
Textbook Question
Draw the product(s) you'd expect when each of these alkenes is treated first with O3, then with CH3SCH3
(d)
3
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Textbook Question
Formation of the molozonide can be expected to proceed stereospecifically. Why is this the case? Show the two different molozonides you would expect to get from ozonolysis of (E)- and (Z)-3,4-dimethylhept-3-ene.
2
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Textbook Question
Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene.
(a)
Textbook Question
What product results when the following molecules are treated with H₂ Pd/C? Be sure to indicate the relative stereochemical outcome. Draw both enantiomers of any racemic mixtures. [It is difficult to control the stoichiometry of gases so there is enough H₂ to reduce all alkenes.]
(b)
1
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Textbook Question
In Solved Assessment 9.30(b), we came up with an alkene that under the conditions of ozonolysis would produce acetophenone and acetaldehyde. There is one other alkene that should produce the same compounds under these conditions. Which is it?