Concept explainers
Interpretation:
A reasonable series of synthetic transformations for converting
Concept Introduction:
Alkyl sulfonates are prepared by the reaction of an alcohol with methyl sulfonyl chlorides. These reactions are carried out in suitable solvents such as trimethylamine,
In these reactions, the hydrogen atom of the hydroxyl group in alcohols is substituted by the methyl sulfonate group.
Their preparation involves the oxygen of the alcohol and not the carbon to which the oxygen is attached.
The stereochemistry of the original alcohol and the carbon skeleton both are maintained when the alcohols are converted to their corresponding alkyl sulfonates.
If the structure for the product molecule is known, then the corresponding reactant alcohol can be found out by replacing the methyl sulfonate group by the hydrogen atom without changing the stereochemistry of the alcohol molecule.
The reaction of this methane sulfonate with sodium acetate in acetic acid produces the corresponding alkyl acetate and this reaction follows the
Alcohols are converted to corresponding
Alkenes are converted into alcohols using hydroboration-oxidation. This reaction produces less substituted alcohol as a major product.
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Chapter 6 Solutions
EBK ORGANIC CHEMISTRY
- On being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) produced a mixture of two alkenes B and C, each of which had the molecular formula C7H14. Catalytic hydrogenation of major isomer B or minor isomer C gave only 3-ethylpentane. Suggest structures and mechanisms for compounds A, B, and C consistent with these observations.arrow_forward1. Compound A, C9H12, absorbs 3 equivalents of H2 on catalytic hydrogenation over palladium catalyst to give B, C9H18. On the treatment with acidic KMnO4, compound A gives among other things, a ketone that was identified as cyclohexanone. On reaction with NaNH2 in NH3, followed by addition of iodomethane, compound A gives a new hydrocarbon C, C10H14. What are the structures of A , B and C?arrow_forwardProvide a mechanism which explains the following conversions. Include all intermediates (where appropriate) and watch your arrows and chargesarrow_forward
- we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?arrow_forwardProvide the structure of the major organic product of the following reaction and? explain the stereochemistry which results in this product. 2-Pentanol reacting with 1.) PBr3, pyridine 2.) NaCNarrow_forwardWhen 1,2-cyclohexanediol is dehydrated in the presence of concentrated sulfuric acid, the major product is not an alkene. Instead, you get cyclohexanone. Write a reasonable and detailed mechanism for the dehydration of 1,2-cyclohexanediol to form cyclohexanone. Use curved arrows to show the flow of electrons and draw the structures of all intermediates and byproducts formed in the course of this reaction as well as any alternative resonance structures that will help you to account for the formation of the major product observed in this reaction.arrow_forward
- Dehydrohalogenation of 1-chloro-1-methylcyclopropane affords two alkenes (A and B) as products. Explain why A is the major product despite the fact that it contains the less substituted double bond.arrow_forwardGive a detailed reaction mechanism for the reaction expected to occur when 2-bromo-2-methylpentane is heated with sodium methoxide. Draw clear structural formulas of all relevant species and use curved arrows to represent electron flow. Discuss the stability of the final compoundarrow_forwardTwo isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data?arrow_forward
- Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. What is the isometric pair of A and B that corresponds?arrow_forwardWhen 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether, the product is analyzed to be C5H10O. Propose a likely structure for this product, suggesting a reasonable mechanistic pathway for its formationarrow_forwardCompound A (C9H12) absorbed 3 equivalents of H2 on catalytic reduction over a palladium catalyst to give B(C9H18). On ozonolysis, compound A gave, among other things, a ketone that was identified as cyclohexanone. Ontreatment with NaNH2 in NH3, followed by addition of iodomethane, compound A gave a new hydrocarbon, C(C10H14 ) . What are the structures of A, B, a nd C?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningGeneral, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage LearningOrganic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,