Concept explainers
Interpretation:
The experiment using an isotopically labeled alcohol that would prove that the formation of an alkyl sulfonate does not cause cleavage at the C–O bond of the alcohol is to be suggested.
Concept introduction:
Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.
Nucleophiles are electron rich species that have negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.
Free radical is an atom, molecule, or ion that has unpaired electrons, which makes it highly chemically reactive.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a
Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
Kinetic isotope study is a method of ascertaining the mechanism of reactions. There are two types of kinetic isotope studies—primary kinetic isotope studies and secondary kinetic isotope studies.
Primary kinetic isotope study evaluates the change in rate of the reaction when an atom in a bond is isotopically substituted, gets cleaved as compared to a bond containing regular isotope that gets cleaved during the course of the reaction (rate limiting as well as subsequent product determining steps). The bond substituted with the heavier isotope vibrates slower and hence, is more stable. The more stable bond requires more energy to cleave and thus slows the
The rates of reaction (or the value of rate constant) do not change on replacing regular 12C–O bond of the alcohol with 13C–O, then this would prove that the bond stays unbroken during the formation of alkyl sulfonate from alcohol.
Want to see the full answer?
Check out a sample textbook solutionChapter 11 Solutions
Organic Chemistry
- (b) Classify the following alcohols in order of increasing ease of acid-catalyzed dehydration. Justify your answers. OH OHarrow_forwardOrganic chemistry:Discuss the Grignard synthesis of triphenyl methanol and benzoic acid .arrow_forwardDevelop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethylcyclopentanearrow_forward
- Give the Grignard reagent and carbonyl compound or ethylene oxide that can be used to prepare the following alcohols. Show all pairs of possible combinations. (b) (CH₂)₂C(OH)CH₂CH₂CH₂ CH CH₂CH₂OHarrow_forwardHow do you account for the observed solubility of naphthalene and sodium chloride in water and in ether based on the nature of the bonds that exist in them?arrow_forward1. For each pair of compounds, predict which compound has the higher boiling point. Support your prediction with a valid scientific argument. (a) isopropyl bromide and n-butyl bromide (b) isopropyl chloride and tert-butyl bromide (c) 1-bromobutane and 1-chlorobutanearrow_forward
- 8. (a) Benzene derivatives exhibit medium to strong absorption in UV-region. Explain why aniline and phenoxide ion have strong UV-absorptions.arrow_forwardExplain the following behaviours :(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses.(ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol.arrow_forwardDraw a structural formula for the alcohol formed by treating each alkene with borane in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide, and specify stereochemistry where appropriate. (a) (d) (b) (e) (c)arrow_forward
- Explain the following observations :(i) The boiling point of ethanol is higher than that of methoxymethane.(ii) Phenol is more acidic than ethanol.(iii) o- and p-nitrophenols are more acidic than phenol.arrow_forwardThe boiling point of butan-2-one (80 °C) is signicantly higher than the boiling point of diethyl ether (35 °C), even though both compounds exhibit dipole–dipole interactions and have comparable molecular weights. Offer an explanation.arrow_forward12.19f Identify the reagent(s) you could use to accomplish the following transformation. Select all that apply. OH NaBr PBr3 1) TsCl, py; 2) PBr3 HBr 1) TsCl, py; 2) NaBr Save for Later Br Attempts: 0 of 3 used MacBook Air Submit Ararrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY