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- Nitriles, R–=C≡N, undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH3CH2C≡N, if it has IR absorptions from 2500–3100 cm-1 and at 1710 cm-1, and has M+=74?arrow_forwardKetones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+=74 in the mass spectrum?arrow_forwardIdentify the structure of compound C (molecular formula C11H15NO2), which has an IR absorption at 1699 cm−1 and the 1H NMR spectrum shown below.arrow_forward
- The azo compound shown below has a λmax value of 410 nm. When treated with hydrogen in the presence of palladium on carbon, the λmax changes significantly. Suggest a reason for this observation and predict whether the λmax value increases or decreases.arrow_forwardDetermine reagents C and D from the reaction scheme below. Choose two (2) answers. Select one or more: H2O, Δ Cl2, CCl4 HCl H2SO4, Δ Cl2, H2Oarrow_forwardWhich is the expected product of the reaction shown?arrow_forward
- 1,3,5,7-Cyclooctatetraene, CgHg, is an unusual hydrocarbon in that it reacts with exactly 2 equivalents of potassium to give A, CgHgK₂, which can be isolated as a white solid. A exhibits a single proton NMR signal. Draw the structure of A. 1,3,5,7-cycloctatetraene 2 K/THF C8H8K2 + H₂ A • Draw cations and anions in separate sketchers. Separate structures with + signs from the drop-down menu. ? n ChemDoodle®arrow_forwardhelp with thisarrow_forward● ● ● ● (A) Cl₂ CH₂=CHCH3 heat Propene OH HOCH₂CHCH₂OH 1,2,3-Propanetriol (glycerol, glycerin) Provide structures for all intermediate compounds (A-D) and describe the type of mechanism by which each is formed. (B) 2A (C₂H₂C1) CI a C (C₂H₂C1O₂) *85 H H₂C=C All hydrogen atoms are implied. Apply formal charges where appropriate. Omit lone pairs and radical electrons from your answer. You do not have to consider stereochemistry. C-Cl H₂ NaOH, H₂O internal displacement Lindlar reduction SN1-substitution SN2-substitution acid-catalyzed hydrolysis addition-elimination allylic halogenation halohydrination vinylic halogenation H H₂C=C Ca(OH)2 D (C3H6O₂) heat → B (C₂H₂O) 00 OU Cl₂, H₂O در H₂O, HCI 2 ster n ? ChemDoodle [Refere ?arrow_forward
- 5arrow_forwardWhen 2-bromo-3,3-dimethylbutane is treated with K+ −OC(CH3)3, a single product T having molecular formula C6H12 is formed. When 3,3dimethylbutan-2-ol is treated with H2SO4, the major product U has the same molecular formula. Given the following 1H NMR data, what are the structures of T and U? Explain in detail the splitting patterns observed for the three split signals in T. 1H NMR of T: 1.01 (singlet, 9 H), 4.82 (doublet of doublets, 1 H, J = 10, 1.7 Hz), 4.93 (doublet of doublets, 1 H, J = 18, 1.7 Hz), and 5.83 (doublet of doublets, 1 H, J = 18, 10 Hz) ppm 1H NMR of U: 1.60 (singlet) ppmarrow_forwardIdentify the following reactions as either SN1, SN2, E1, or E2: (a) Br CHCH3 CH=CH2 КОн (b) Br OCH3 CHCH3 .CHCH3 CH3OH Нeatarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning