Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 13.8D, Problem 13.9P
- a. Assign protons to the peaks in the NMR spectrum of 4,4-dimethylcyclohex-2-en-1-one in Figure13-30(a). Explain the splitting that gives the triplets at δ 1.8 and δ 2.4.
- b. Assign protons to the peaks in the NMR spectrum of β - ionone in Figure13-30(b). Explain the splitting seen in the three multiplets at δ 1.5, δ 1.65, and δ 2.1. Explain how you know which of these multiplets corresponds to which methylene groups in the molecule.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Make a sketch of the partial mass spectrum of 1-bromoheptane, showing the position of
the peaks for: [Masses: H=1; C=12; Br=79 and Br=81 (isotopes)]
i) The Molecular ion(s)
ii) The fragments resulting from a split between carbons 3 and 4.
iii) The fragments resulting from a split between carbons 5 and 6.
Annotate the Mass Spec, 1H NMR, and 13C NMR for C5H12O or Pentan-2-ol
Account for the formation of the base peaks in these mass spectra.
Q.) Isobutylmethylamine, m/z 44
Chapter 13 Solutions
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
Ch. 13.5A - In a 300-MHz spectrometer, the protons in...Ch. 13.5B - Prob. 13.2PCh. 13.6 - Determine the number of different kinds of protons...Ch. 13.6 - Prob. 13.4PCh. 13.7 - Draw the integral trace expected for the NMR...Ch. 13.7 - Prob. 13.6PCh. 13.8C - Draw the NMR spectra you would expect for the...Ch. 13.8D - Draw the NMR spectra you expect for the following...Ch. 13.8D - a. Assign protons to the peaks in the NMR spectrum...Ch. 13.8D - Prob. 13.10P
Ch. 13.8D - Two spectra are shown. Propose a structure that...Ch. 13.9 - Prob. 13.12PCh. 13.9 - The spectrum of trans-hex-2-enoic acid follows. a....Ch. 13.9 - Prob. 13.14PCh. 13.9 - Prob. 13.15PCh. 13.10 - Prob. 13.16PCh. 13.10 - If the imaginary replacement of either of two...Ch. 13.10 - Predict the theoretical number of different NMR...Ch. 13.11B - Prob. 13.19PCh. 13.11B - Prob. 13.20PCh. 13.11B - Prob. 13.21PCh. 13.11B - Prob. 13.22PCh. 13.11B - Prob. 13.23PCh. 13.11B - Prob. 13.24PCh. 13.12E - Draw the expected broadband-decoupled 13 C N M R...Ch. 13.12E - a. Show which carbon atoms correspond with which...Ch. 13.12E - Repeat Problem13-25, sketching the...Ch. 13.12F - Prob. 13.28PCh. 13.13 - A bottle of allyl bromide was found to contain a...Ch. 13.13 - A laboratory student was converting cyclohexanol...Ch. 13.14 - Sets of spectra are given for two compounds. For...Ch. 13 - An unknown compound has the molecular formula C 9...Ch. 13 - Prob. 13.34SPCh. 13 - Predict the approximate chemical shifts of the...Ch. 13 - Prob. 13.36SPCh. 13 - Prob. 13.37SPCh. 13 - Prob. 13.38SPCh. 13 - Prob. 13.39SPCh. 13 - Prob. 13.40SPCh. 13 - For each compound shown below. 1. sketch the 13 C...Ch. 13 - Prob. 13.42SPCh. 13 - Prob. 13.43SPCh. 13 - Prob. 13.44SPCh. 13 - Prob. 13.45SPCh. 13 - Prob. 13.46SPCh. 13 - A compound was isolated as a minor constituent in...Ch. 13 - Prob. 13.48SPCh. 13 - The three isomers of dimethylbenzene are commonly...Ch. 13 - a. Draw all six isomers of formula C 4 H 8...Ch. 13 - Prob. 13.51SPCh. 13 - Hexamethylbenzene undergoes free-radical...Ch. 13 - Each of these four structures has molecular...Ch. 13 - Prob. 13.54SPCh. 13 - Phenyl Grignard reagent adds to 2-methylpropanal...Ch. 13 - Prob. 13.56SP
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
- 9- Draw the 1H NMR spectrum of Ethyl bromide or 2-Chloropropane. Show the splittingindicating which is singlet, which is doublet, etc.arrow_forwardLabel the 13C spectrum of (R,R)-N,N’-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine peaks and explain why they appear at the ppm that they show up at.arrow_forwardWhat are the functional groups in Camphor and Isoborneol? What peaks show up in their respective IR spectrum + wavenumber (cm-1)arrow_forward
- Following is a 1H-NMR spectrum of 2-butanol. Explain why the CH2 protons appear as a complex multiplet rather than as a simple quintet.arrow_forwardExplain the order of chemical shifts of the carbon atoms in the 13C spectra of cyclohexanone (fig 22.6 ) and adipic acid (fig .22.9) attached below .arrow_forwardA graduate student was following a procedure to make 3-propylcyclohexa-1,4-diene. He overheated the product. He isolated the product, which gave the appropriate =C−H stretch in the IR, but the C=C stretch appeared around 1630 cm−1as opposed to the literature value of 1650 cm−1for the desired product. The mass spectrum showed the correct molecular weight, but the base peak was at M–29 rather than at M–43 as expected. Because of the anomalous IR spectrum, he took a UV spectrum that showed λmaxat 261 nm. c) Draw the structure of the desired product and propose a structure for the actual product d) Show why he expected the MS base peak to be at M–43, and show how your proposed structure would give an intense peak at M–2arrow_forward
- Assume that you are carrying out the base-induced dehydrobromination of 3-bromo-3-methylpentane (Section 11-7) to yield an alkene. How could you use IR spectroscopy to tell which of three possible elimination products is formed, if one includes E/Z isomers?arrow_forwardPlease help me correct the peak integrations and multiplicities of the H-NMR for 1-Bromo-2-Hexene.arrow_forwardDetermine the Ksp of the following reactions. a. NaC2H3O2 ⇄ Na+ + C2H3O2- b. HBr⇄H++Br c. Zn(OH)2 ⇄ Zn+2 + 2HO-arrow_forward
- Use equations to explain the prominent peaks at m>z 74 and m>z 87 in the mass spectrumof 2-methylpentanoic acidarrow_forwardChoose the structure that best fits this DEPT-135 spectrum.arrow_forwardProvide a structure that is consistent with the data below: - C6H12O2 - IR (cm-1): 2880-2980, 1738(strong) - 1HNMR (ppm): 5.0(1H, sept), 2.3(2H, q), 1.2(6H, d), 1.1 (3H, t)13 - CNMR (ppm)(proton coupled, DEPT): 174(s, none), 67(d, positive), 28(t, negative), 21(q, positive), 9(q, positive) (The attached image to this question is an incorrect answer, please identify the mistakes made in the given answer and please explain how to get the correct answer. )arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENTMacroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY