(a)
To determine: The actual oxidizing agent and the function of the other reagents.
Interpretation: The actual oxidizing agent is to be identified and the function of other reagents is to be stated.
Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield
(b)
To determine: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product.
Interpretation: An explanation corresponding to the fact that Sharpless epoxidation gives only one pure enantiomer of the product is to be stated.
Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield
(c)
To determine: The other enantiomer of the product.
Interpretation: The other enantiomer of the product is to be stated.
Concept introduction: In catalytic asymmetric synthesis, an achiral starting material is converted into mostly one enantiomer of a chiral product. An asymmetric epoxidation of allylic alcohols yield
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EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
- Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*arrow_forwardEthers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of iodoethane with the following alkoxide ion: H3C CH3 + Na You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I, in your answer. P opy aste [*arrow_forwardA problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_forward
- What is the major monosubstitution product from the Friedel—Crafts reaction of benzene with 1 -chloro-2-methylpropane in the presence of AlCl3?arrow_forwardBromine reacts with alkenes in methanol according to the equation when this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield). Which of the following is the structure more reasonable for this compound? Explain your reasoning through a corresponding mechanism.arrow_forwardYou are trying to monobrominate methylcyclopentane to form a compound with the molecular formula C6H11Br. Using the relative reactivities for bromination in the picture, calculate the percentages of each isomer expected for this reaction.arrow_forward
- Draw the alkene that would react with the reagent given to account for the product formed. CH3 HCI CH3 CHCCH, ? + Či CH3 You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.arrow_forwardThe synthesis of carbohydrates can be particularly difficult because of the large number of chiral centers and OH functional groups present. Epoxides can be useful synthetic intermediates in carbohydrate synthesis. Draw the product of the reaction of a phenyl Gilman reagent with this epoxide. A • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Explicitly define the cis/trans stereochemistry of fused rings using wedge or hash bonds. • If enantiomers are formed, draw both. • Separate multiple products using the + sign from the drop-down menu.arrow_forwardNAME and DRAW the STRUCTURE of ALL the alkenes which could undergo catalytic hydrogenation at 900°C to form methylcyclopentane. Circle the alkene with the HIGHEST stability and X the alkene with the HIGHEST heat of hydrogenation. Give reasons for your choice.arrow_forward
- Draw the structural formula of the major product of the reaction of (S)-2,2,3-trimethyloxirane with Me,NH. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. • If a group is achiral, do not use wedged or hashed bonds on it.arrow_forwardFill in the following missing organic structures. Consider stereochemistry (R/S and/or E/Z –cis/trans) and possible carbocation rearrangements.arrow_forwardConsider the monosubstituted benzene reagent X. Nitration of X yields product Y. Product Y is analysed by 1H and 13C NMR spectroscopy (see Figures 1 to 4). Determine the structure of X and Y on the basis of the spectral data provided.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning