Problem 10.65 is intended for students who have already learned about spectroscopy in Chapters A-C. 10.65 When 2-bromo-3,3-dimethylbutane is treated with K+ OC(CH3)3, a single product T having molecular formula C6H12 is formed. When 3,3- dimethylbutan-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

Problem 10.65 is intended for students who have already learned about spectroscopy in Chapters A-C. 10.65 When 2-bromo-3,3-dimethylbutane is treated with K+ OC(CH3)3, a single product T having molecular formula C6H12 is formed. When 3,3- dimethylbutan-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

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.57P

See similar textbooks

Similar questions

Part 5a. Rotamers. Answers the following questions about the C-C bond indicated below 3 4 3-methylhexane H/H eclipsed CH3/H eclipsed CH3CH₂/H eclipsed CH3/CH3 eclipsed CH3/CH₂CH3 eclipsed CH₂CH3/CH₂CH3 eclipsed CH3/CH3 gauche CH3CH₂CH3 gauche CH₂CH3/CH₂CH3 gauche 1.0 kcal/mol 1.5 kcal/mol 1.6 kcal/mol 2.5 kcal/mol 3.0 kcal/mol 5.1 kcal/mol 0.9 kcal/mol unknown 1.6 kcal/mol (a) Draw the most stable rotamer, using a newman projection, for the C3-C4 bond of 3- methylhexane. (b) Draw the least stable rotamer, using a newman projection, for the C3-C4 bond of 3-methyl hexane. (c) The barrier to rotation for the C3-C4 bond of 3-methylhexane is 6.3 kcal/mol. Given this information, and the information provided above, what is the energy cost for a CH3 / CH₂CH3 gauche interaction? (show your work)
Ω Enilconazole CH₂ Enilconazole is an agricultiral fungicide. Synthesis of enilconazole involves an SÃ2 reaction between an alkoxide ion and a secondary alkyl chloride. Draw the structures of these components if the chirality of the resulting ether is (R).
6:06 PM 4G 49 ll PROBLEM SET – ETHER 1. Name the following ethers by IUPAC rules: (a) CH3 CH3 (b) -OCH;CH,CH3 CH3CHOCHCH3 (c) .OCH3 (d) CH3 CH3CHCH2OCH,CH3 Br
Arrange the following groups in order of increasing priority. Q.) -CH3 -CH2OH -CH2NH2 -CH2Br
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.
8. Predict which member of each pair will be more soluble in water. Explain why! (i) Hexane-1-ol and cyclohexanol (ii) Heptan-1-ol and 4-methylphenol (iii) Two isomers of glyceraldehyde. H. H H-C-OH OH-C-H CH₂OH CH₂OH
Draw the organic product(s) of the following reaction. CH3 H3C-C-CEC-H CH3 NaOC2Hs / CH5OH 1 eq. NANH2, NH3(1) CH;CH,CH,CH2-Br H-CEC-H H;C CH-Br H3C 1 eq. NaNH2, NH3() H3C-CEC-H
(a) 2-methyl-2-pentanol Draw the structure of the alkene that was used to prepare the alcohol in highest yield. AAVIL ? ChemDoodleⓇ Which process does this employ? 1. Hg(OAc)2, H₂O; 2. NaBH4 01. BH3; 2. H₂O2, NaOH OsO4, H₂O2 On n [ ]#
2-Methyl-2-butanol reacts rapidly with aqueous HCI to give A (C5H₁1CI). Treatment of A with KOH in alcohol gives B (C5H10) as the major product. Draw the structure of B. O • You do not have to consider stereochemistry. • In cases where there is more than one answer, just draw one. ChemDoodleⓇ
Draw the products formed when (CH3)2C=CH2 is treated with each reagent.a. HBrb. H2OH2SO4c. CH3CH2OH, H2SO4d. Cl2e. Br2, H2Of. NBS (aqueous DMSO)g. [1]BH3;[2]H2O2, HO-
Which reaction will produce this alkene as the major product? A. A B. B C. Both D. Neither (a) (b) Br NaOCH3 Δ H₂C P(Ph)3
An alkene G (C6H12) reacts with cold basic KMnO4 to produce H (C6H14O2). Hydrogenation of Gproduces I (C6H14). Ozonolysis of G produces propanone (CH3COCH3) and propanal(CH3CH2CHO).a) Draw the structure of G, H, I.b) State the reagent(s) and condition for ozonolysis reaction