Concept explainers
Interpretation:
The structure of the major stereoisomer formed in the reaction of
Concept Introduction:
>In epoxidation of alkenes, peroxyacids transfer oxygen to the double bond of alkenes to form a three membered oxygen containing ring called as
Peroxyacid prefers to attack the less sterically hindered face of the double bond in orderto form corresponding epoxides.
>Diastereomers are the non-mirror images of each other having opposite absolute configuration at only one chiral carbon atom.
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ORGANIC CHEM BUNDLE >BI<
- When (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH,nucleophilic substitution yields an optically inactive solution. When theisomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OHunder the same conditions, nucleophilic substitution forms an opticallyactive solution. Draw the products formed in each reaction, and explainwhy the difference in optical activity is observed.arrow_forwardWhen (ft)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (fl)-2-bromo-2,5- dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.arrow_forwardWhen attached halohydrin is treated with NaH, a product of molecular formula C4H8O is formed. Draw the structure of the product and indicateits stereochemistry.arrow_forward
- When attached halohydrin is treated with NaH, a product of molecularformula C4H8O is formed. Draw the structure of the product and indicateits stereochemistry.arrow_forwardClopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in patients that have a history of heart attacks or strokes. A single enantiomer of clopidogrel can be prepared in three steps from the chiral αhydroxy acid A. Identify B and C in the following reaction sequence, and designate the conguration of the enantiomer formed by this route as R or S.arrow_forwardOxidation of cholesterol converts the alcohol to a ketone. Under acidic or basic oxidationconditions, the C“C double bond migrates to the more stable, conjugated position. BeforeIR and NMR spectroscopy, chemists watched the UV spectrum of the reaction mixture tofollow the oxidation. Describe how the UV spectrum of the conjugated product, cholest-4-en-3-one, differs from that of cholesterolarrow_forward
- Draw the products formed when both cis- and trans-but-2-ene are treated with a peroxyacid followed by -OH (in H2O).Explain how these reactions illustrate that anti dihydroxylation is stereospecic.arrow_forwardWhen pure (S)-lactic acid is esterified by racemic butan-2-ol, the product is 2-butyl lactate, with the following structure:H+CH3 CH COOH CH3 CH CH3 CH CHOH OHCH2CH3 CH2CH3lactic acidC OOH CH O 3butan-2-ol 2-butyl lactate+(a) Draw three-dimensional structures of the two stereoisomers formed, specifying the configuration at each asymmetriccarbon atom. (Using your models may be helpful.)(b) Determine the relationship between the two stereoisomers you have drawnarrow_forwardAn acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2phenylpropanoic acid forms two products having different melting points and somewhat different solubilities. Draw the structure of these two products. Assign R and S to any stereogenic centers in the products. How are the two products related? Choose from enantiomers, diastereomers, constitutional isomers, or not isomers of each other.arrow_forward
- Treatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.arrow_forwardDraw the product formed when the following compound undergoes an intramolecular Heck reaction. Indicate the stereochemistry at all double bonds and tetrahedral stereogenic centers.arrow_forwardTreatment of compound A (C8H17Br) with NaOCH2CH3 affords two constitutional isomers B and C. Ozonolysis of B affords CH2=O and (CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 and CH3CH2CHO. What is the structure of A?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning