EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 8220100591310
Author: McMurry
Publisher: CENGAGE L
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 17.11, Problem 19P
When the 1HNMR spectrum of an alcohol is run in dimethylsulfoxide (DMSO) solvent rather than in chloroform, exchange of the Ο-H proton is slow and spin-spin splitting is seen between the Ο-H proton and C-H protons on the adjacent carbon. What spin multiplicities would you expect for the hydroxyl protons in the following alcohols?
(a) 2-Methyl-2-propanol
(b) Cyclohexanol
(c) Ethanol
(d) 2-Propanol
(e) Cholesterol
(f) 1-Methylcyclohexanol
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Briefly state the electrocapillary equation for ideally polarized electrodes.
What is surface excess according to the Gibbs model?
Using Benzene as starting materid show
how each of the Following molecules Contel
Ve syntheswed
CHI
9.
b
-50311
с
CHY
503H
Ночто
d.
อ
•NOV
e
11-0-650
NO2
Chapter 17 Solutions
EBK ORGANIC CHEMISTRY
Ch. 17.1 - Give IUPAC names for the following compounds:Ch. 17.1 - Prob. 2PCh. 17.2 - The following data for isomeric four-carbon...Ch. 17.2 - Rank the following substances in order of...Ch. 17.2 - Prob. 5PCh. 17.3 - Prob. 6PCh. 17.4 - What reagent would you use to accomplish each of...Ch. 17.4 - Prob. 8PCh. 17.5 - Prob. 9PCh. 17.5 - Prob. 10P
Ch. 17.5 - Use the reaction of a Grignard reagent with a...Ch. 17.6 - How would you carry out the following...Ch. 17.6 - What products(s) would you expect from dehydration...Ch. 17.7 - What alcohols would give the following products on...Ch. 17.7 - What products would you expect from oxidation of...Ch. 17.8 - TMS ethers can be removed by treatment with...Ch. 17.9 - Show the mechanism for the reaction of...Ch. 17.11 - Prob. 18PCh. 17.11 - When the 1HNMR spectrum of an alcohol is run in...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw the structure of the carbonyl compound(s)...Ch. 17.SE - Prob. 22VCCh. 17.SE - Prob. 23VCCh. 17.SE - Name and assign R or S stereochemistry to the...Ch. 17.SE - Evidence for the intermediate carbocations in the...Ch. 17.SE - Acid-catalyzed dehydration of 2,...Ch. 17.SE - Prob. 27MPCh. 17.SE - Treatment of the following epoxide with aqueous...Ch. 17.SE - Prob. 29MPCh. 17.SE - Prob. 30MPCh. 17.SE - Identify the type of substitution mechanism (SN1,...Ch. 17.SE - The conversion of 3 alcohols into alkenes under...Ch. 17.SE - Prob. 33MPCh. 17.SE - The trimethylsilyl (TMS) protecting group is one...Ch. 17.SE - When the alcohol below is treated with POCI3 and...Ch. 17.SE - Phenols generally have lower pKa’s than...Ch. 17.SE - Give IUPAC names for the following compounds:Ch. 17.SE - Draw and name the eight isomeric alcohols with...Ch. 17.SE - Prob. 39APCh. 17.SE - Named bombykol, the sex pheromone secreted by the...Ch. 17.SE - Carvacrol is a naturally occurring substance...Ch. 17.SE - What Grignard reagent and what carbonyl compound...Ch. 17.SE - What carbonyl compounds would you reduce to...Ch. 17.SE - What carbonyl compounds might you start with to...Ch. 17.SE - Prob. 45APCh. 17.SE - What products would you obtain from reaction of...Ch. 17.SE - Prob. 47APCh. 17.SE - How would you prepare the following compounds from...Ch. 17.SE - Prob. 49APCh. 17.SE - What products would you expect to obtain from...Ch. 17.SE - Prob. 51APCh. 17.SE - Propose structures for alcohols that have the...Ch. 17.SE - Propose a structure consistent with the following...Ch. 17.SE - The 1HNMR spectrum shown is that of...Ch. 17.SE - A compound of unknown structure gave the following...Ch. 17.SE - Propose a structure for a compound C15H24O that...Ch. 17.SE - Prob. 57APCh. 17.SE - Prob. 58APCh. 17.SE - Rank the following substituted phenols in order of...Ch. 17.SE - Benzvl chloride can be converted into benzaldehvde...Ch. 17.SE - Prob. 61APCh. 17.SE - Prob. 62APCh. 17.SE - Prob. 63APCh. 17.SE - Prob. 64APCh. 17.SE - Prob. 65APCh. 17.SE - Prob. 66APCh. 17.SE - Dehydration of trans-2-methylcyclopentanol with...Ch. 17.SE - 2, 3-Dimethyl-2, 3-butanediol has the common name...Ch. 17.SE - As a rule, axial alcohols oxidize somewhat faster...Ch. 17.SE - Prob. 70APCh. 17.SE - A problem often encountered in the oxidation of...Ch. 17.SE - Identify the reagents a-f in the Following scheme:Ch. 17.SE - Prob. 73APCh. 17.SE - Prob. 74APCh. 17.SE - Compound A, C8H10O, has the IR and 1H NMR spectra...Ch. 17.SE - Prob. 76APCh. 17.SE - Prob. 77AP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- The molecule PYRIDINE, 6th electrons and is therefore aromatre and is Assigned the Following structure contering Since aromatk moleculoy undergo electrophilic anomatic substitution, Pyridine shodd undergo The Following reaction + HNO3 12504 a. write all of the possible Mononitration Products that could Result From this reaction 18. Bared upon the reaction mechanison determime which of these producty would be the major Product of the hegetionarrow_forwarda. Explain Why electron withdrawing groups tend to be meta-Directors. Your answer Should lyclude all apropriate. Resonance contributing Structures fo. Explain why -ll is an outho -tura drccton even though chlorine has a very High Electronegativityarrow_forward9. Write Me product as well as the reaction Mechanism For each of the Following Vanctions +H₂504 4.50+ T C. +212 Fellz 237 b. Praw the potential energy Diagrams For each OF Mese Rauctions and account For any differences that appear in the two potential Puergy Diagrams which of here two reactions 19 Found to be Reversable, Rationalice your answer based upon the venation mechanisms and the potential energy diagrams.arrow_forward
- 9. Write Me product as well as the reaction Mechanism For each of the Following Veritious +H2504 4.50+ + 1/₂ Felly ◎+ 7 b. Praw he potential energy Diagrams For each OF Mese Ronctions and account for any differences that appeak in the two potential Puergy Diagramsarrow_forwardDraw the major product of this reaction. Ignore inorganic byproducts. Incorrect, 3 attempts remaining 1. excess Br2, NaOH 2. neutralizing workup Qarrow_forwardGiven the electrode Pt | Ag | Ag+ (aq), describe it.arrow_forward
- At 25°C, the reaction Zn2+ + 2e ⇄ Zn has a normal equilibrium potential versus the saturated calomel electrode of -1.0048 V. Determine the normal equilibrium potential of Zn versus the hydrogen electrode.Data: The calomel electrode potential is E° = 0.2420 V versus the normal hydrogen electrode.arrow_forwardElectrochemistry. State the difference between E and E0.arrow_forwardIn an electrolytic cell, the positive pole is always assumed to be on the right side of the battery notation. Is that correct?arrow_forward
- In an electrolytic cell, the positive pole is always assumed to be on the right side of the battery. Is that correct?arrow_forwardCalculate the free energy of formation of 1 mol of Cu in cells where the electrolyte is 1 mol dm-3 Cu2+ in sulfate solution, pH 0. E° for the Cu2+/Cu pair in this medium is +142 mV versus ENH.Assume the anodic reaction is oxygen evolution.Data: EH2 = -0.059 pH (V) and EO2 = 1.230 - 0.059 pH (V); 2.3RT/F = 0.059 Varrow_forwardIf the normal potential for the Fe(III)/Fe(II) pair in acid at zero pH is 524 mV Hg/Hg2Cl2 . The potential of the saturated calomel reference electrode is +246 mV versus the NHE. Calculate E0 vs NHE.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Physical ChemistryChemistryISBN:9781133958437Author:Ball, David W. (david Warren), BAER, TomasPublisher:Wadsworth Cengage Learning,
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Physical Chemistry
Chemistry
ISBN:9781133958437
Author:Ball, David W. (david Warren), BAER, Tomas
Publisher:Wadsworth Cengage Learning,
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY