Interpretation:
Reactants X and product Y in the given sequence of reactions is to be determined.
Concept Introduction:
Alkyl sulfonates are prepared by the reaction of an alcohol with 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 comprises 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, the corresponding reactant alcohol can be found 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 azide produces the corresponding alkyl azide, and this reaction follows the
Want to see the full answer?
Check out a sample textbook solutionChapter 6 Solutions
Organic Chemistry - Standalone book
- (a) Analyze SNl or Sx2 is preferred in the reaction below. Explain your choice and express the mechanisms. Br OCH, HBr CH,OH (b) Predict the following nucleophiles in order of increasing reactivity towards CH:CH:Br in the polar aprotic solvent, such as acetone. Explain your answer. F Brarrow_forwardThe following reaction gives a mixture of the nucleophilic substitution (SN1 or SN2) and elimination (E1 or E2) products. Propose two mechanisms that can account for the formation of these products. One mechanism should be for the nucleophilic substitution reaction and the other mechanism would show the elimination reaction.arrow_forwardIn the chemical reaction between 2-chloro-2-methyl-propane and ethanolic silver nitrate solution, a precipitate is definitely formed. Using the skeletal structures of the molecules, write out the skeletal structure of each reaction (don't include the mechanism). Identify what the nucleophile is in each type of reaction, especially within this SN1 reaction. Explain the reactivity of each electrophile/substrate in terms of whether they are tertiary, secondary, primary, etc. for each reaction. Include the overall chemical reaction.arrow_forward
- 8A In the following compounds indicate with an arrow or arrows the position or positions in aromatic ring which will undergo an electrophilic aromatic reaction substitution. Justify your answer (i) NC. OCH 3 (il) Oarrow_forwardChoose from the options A-E and explain briefly by illustrations the chemistry behind each answer. Preamble: A reaction flask contains a 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and results in the formation of two olefinic 1.All the following parameters would affect the rate and kinetics of the reaction exceptA.Solvent mediumB.Reaction temperatureC.Reaction timeD.Geometry and structure of the alkyl halideE.pH 2.What would be the major product when 2-iodopentane is involved in a dehydrohalogenation reaction? A.2-iodo-1-penteneB.2-penteneC.(E)-2-penteneD.(Z)-2-penteneE.Cis-2-pentenearrow_forward(b) Predict the major product (or products) formed when each of the following compounds 11- 14 reacts with a mixture of concentrated HNO3 and H2SO4. CO2H HN CO2H CI 11 12 13 14 (c) Pick one of the reactions under (b) and write the mechanism of the electrophilic aromatic substitution in detail (generation of the attacking electrophile is not required).arrow_forward
- Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev’s rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak…arrow_forwardDescribe the mechanism by which benzene is converted to bromobenzene (C6H5Br) on treatment with a mixture of bromine and iron (III) bromide (Br2/FeBr3). Your answer should illustrate how the electrophile (Br*) is formed from the Br₂/FeBr3 and how it is involved in the electrophilic substitution of the aromatic ring.arrow_forwardAlkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev’s rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak…arrow_forward
- The rate constants for the bromination of several disubstituted stilbenes are given in the table below. Given that the double bond of stilbene acts as the nucleophile, provide a reasonable explanation for the trend observed among the rate constants. X -OMe -OMe -OMe -OMe oooo Br2 121 Y -OMe Me -Cl -NO₂ Br Br k(x103 1/mol-min) 220 114 45 5.2arrow_forwardThe sodium iodide test is used to identify primary alkyl halides and it also takes place via a substitution reaction.Describe the test including the reactions that explain the full mechanism. Explain whether this reaction follows aSN1 or a SN2 mechanism.arrow_forwardNucleophilic aromatic substitution involves the formation of a resonance-stabilized carbanion intermediate called a Meisenheimer complex as the nucleophile attacks the ring carbon carrying the eventual leaving group; electron-withdrawing groups ortho and/or para to the site of attack help to stabilize this structure via resonance. For the reaction below, draw the structure of the stabilized reaction intermediate in the box below. CI F3C CF3 NO₂ F3C N CF3 NO₂ • You do not have to consider stereochemistry. • Draw the Meisenheimer complex with a formal charge of 0 on the nucleophilic atom. If more than one resonance structure is possible, only draw the most important one.arrow_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