Concept explainers
Interpretation: An explanation for the given observation that when
Concept introduction: Hydrogen bromide is useful to convert all alcohols
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ORGANIC CHEMISTRY-STUDY GDE...-W/ACCESS
- Explain the following observation. Ethyl 3-phenylpropanoate (C6H5CH2CH2CO2CH2CH3) reacts with electrophiles to afford ortho- and para-disubstituted arenes, but ethyl 3-phenylprop-2-enoate (C6H5CH= CHCO2CH2CH3) reacts with electrophiles to afford meta-disubstituted arenes.arrow_forwardAcid-catalyzed bromination of pentan-2-one (CH3COCH2CH2CH3) forms two products: BrCH2COCH2CH2CH3 (A)and CH3COCH(Br)CH2CH3 (B). Explain why the major product is B, with the Br atom on the more substituted side of the carbonyl group.arrow_forwardThese reagents can produce ketones with alkynes A. BH3, THF, H2O2 B. KMnO4 C. O3 D. H2SO4, H2O, HgSO4 choices:A,DB,CA,B,CA,B,C,Darrow_forward
- When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observedarrow_forwardWhen 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observed.(c) Use a Newman projection of the transition state to predict the major product of elimination of (2S,3R)-2-bromo-3-phenylbutanearrow_forwardExplain how the reaction of (CH3)2CHCH(Cl)CH3 with H2O yields two substitutionproducts, (CH3)2CHCH(OH)CH3 and (CH3)2C(OH)CH2CH3arrow_forward
- Reaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed by treatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 18.arrow_forwardAcid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forwardTreating 4-penten-1-ol with bromine in water forms a cyclic bromoether. Account for the formation of this product rather than a bromohydrin as was formed in Problem 6.33arrow_forward
- The compound 3,4-dimethyl-hexan-3-ol of 3R, 4S configuration is treated with a concentrated HBr solution at room temperature. A mixture of two stereoisomers is obtained.If the reaction mixture above is heated, the appearance of several other compounds is observed. 1) Draw the different compounds obtained using the wedge-flywheel representation. 2) What is the majority product? Explain 3) Propose a modification of the experimental conditions in order to obtain the exclusive formation of these compounds obtained after heatingarrow_forwardWhich of the following reagent best accomplish this transformation below? a. Li/NH3 b. H2SO4, H2O, HgSO4 c. BH3, THF d. potassium permanganatearrow_forwardWhen (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_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning