Guided course 03:19The mechanism of how peroxy acids make epoxides.Johnny Betancourt2639views22rank9comments
Guided course 02:26Halohydrins to epoxides via intramolecular SN2.Johnny Betancourt2564views19rank15comments
Textbook Questiona. Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed. 3. a peroxyacid481views
Textbook QuestionWhat is the major product of the reaction of 2-methyl-2-butene with each of the following reagents? f. MCPBA (a peroxyacid)497views
Textbook QuestionCalculate the atom economy for the reactions shown. In each, what happens to the percentage of material that is not incorporated into the major product?511views
Textbook QuestionPredict the major products of the following reactions. a. cis-hex-2-ene + mCPBA in chloroform673views
Textbook QuestionPredict the products, including stereochemistry where appropriate, for the m-chloroperoxybenzoic acid epoxidations of the following alkenes. c. cis-cyclodecene d. trans-cyclodecene501views
Textbook QuestionPredict the products, including stereochemistry where appropriate, for the m-chloroperoxybenzoic acid epoxidations of the following alkenes. a. cis-hex-2-ene b. trans-hex-2-ene425views
Textbook Question(••) Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (d)357views
Textbook Question(••) Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (h)331views
Textbook Question(••) Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. (h)314views
Textbook Question(••) Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (k)415views
Textbook QuestionPredict the product(s) when each of the following are reacted with mCPBA, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers. (a)473views
Textbook QuestionWhen producing a chiral molecule, epoxide formation still results in a mixture of enantiomers, despite its stereospecificity. (b) How is it that a reaction can be stereospecific while still producing two enantiomers?494views
Textbook Question(•••) Rank the reactivity of the following alkenes with mCPBA ( 1 = most reactive , 5 least reactive ).549views
Textbook Question(••••) One way to think about concerted reactions is to imagine them as being stepwise reactions where, besides the slowest step, all others have infinitesimally small activation energies. Considering the hypothetical stepwise mechanism and actual concerted mechanism of epoxide formation, show what a reaction coordinate diagram might look like for each possibility. (a) Stepwise, hypothetical mechanism:519views
Textbook Question(••••) One way to think about concerted reactions is to imagine them as being stepwise reactions where, besides the slowest step, all others have infinitesimally small activation energies. Considering the hypothetical stepwise mechanism and actual concerted mechanism of epoxide formation, show what a reaction coordinate diagram might look like for each possibility. (b) Concerted , actual mechanism (butterfly transition state:473views
Textbook QuestionHow does the carbonyl in mCPBA weaken the O―O σ bond (i.e., make a better leaving group)?<IMAGE>281views
Textbook QuestionCalculate the atom economy of the reaction in Figure 9.24. [Catalysts are not included in the atom economy calculation.] <IMAGE>255views
Textbook Question(•••) In addition to using mCPBA (Chapter 9), epoxides can be synthesized from alkenes in the two-step process shown. Give a mechanism for each step of the process.<IMAGE>312views
Textbook QuestionPropose mechanisms for the epoxidation and ring-opening steps of the epoxidation and hydrolysis of trans-but-2-ene shown above. Predict the product of the same reaction with cis-but-2-ene. < of reaction>955views
Textbook Question(•••) In Chapter 9, electron-rich alkenes were oxidized under acidic conditions with mCPBA. Conjugated alkenes can be oxidized using the same reagent, but under basic conditions. Suggest a mechanism for this reaction. [Think about what is electron-rich and what is electron-poor in the reaction. Also, identify the bonds formed and broken.]330views
Textbook QuestionPredict the product(s) when each of the following are reacted with mCPBA, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.(d) <IMAGE>332views
Textbook QuestionEvidence for the concertedness of epoxide formation comes from the stereospecificity of the reaction. If step 2 of a hypothetical stepwise mechanism were slow enough to make the reaction non-concerted, how would the product distribution change?<IMAGE>295views
Textbook QuestionWhat alkene would you treat with a peroxyacid in order to obtain each of the epoxides in Problem 27?a. 2-propyloxiraneb. cyclohexene oxide365views
Textbook Questiona. What alkene is required to synthesize each of the following compounds?b. What other epoxide is formed in each synthesis?c. Assign an R or S configuration to each asymmetric center.1. <IMAGE>279views
Textbook Questiona. What alkene is required to synthesize each of the following compounds?b. What other epoxide is formed in each synthesis?c. Assign an R or S configuration to each asymmetric center.2. <IMAGE>273views
Textbook QuestionWhat alkene would you treat with a peroxyacid in order to obtain each of the epoxides in Problem 27?c. 2,2,3,3-tetramethyloxiraned. 2,3-epoxy-2-methylpentane315views
Textbook QuestionMagnesium monoperoxyphthalate (MMPP) epoxidizes alkenes much like mCPBA. MMPP is more stable, however, and it may be safer to use for large-scale and industrial reactions. Propose a mechanism for the reaction of trans-2-methylhept-3-ene with MMPP, and predict the structure of the product(s).<IMAGE>439views
Textbook QuestionLimonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents. <IMAGE>b. m-chloroperoxybenzoic acid267views
Textbook QuestionRetrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. In Chapter 10, we begin developing multistep syntheses in this manner. For now, try to work backward a single step by suggesting an alkene and a reagent that would give products (a)–(i). [Your answers should not include alkenes that undergo rearrangement to give the desired products.]325views
Textbook QuestionPredict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers. A.359views
Textbook QuestionPredict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers. C.440views
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