Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 19.SE, Problem 87AP
The proton NMR spectrum for a compound with formula C10H12O2 is shown below. The infrared spectrum has a strong band at 1711 cm-1. The broadband-decoupled 13C NMR spectral results are tabulated along with the DEPT–135 and DEPT–90 information. Draw the structure of this compound.
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each carbon signal and write out the reaction.
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Deduce the structure of the compound that gives the following 1H, 13C, and IR spectra.
Assign all aspects of the 1H and 13C spectra to the structure you propose. Use letters to
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carbons with the signals in the 13C spectrum. The mass spectrum of this compound shows
the molecular ion at m/z 148.
6H
1H
2H 2H
1H
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Chapter 19 Solutions
Organic Chemistry
Ch. 19.1 - Prob. 1PCh. 19.1 - Draw structures corresponding to the following...Ch. 19.2 - Prob. 3PCh. 19.2 - How would you carry out the following reactions?...Ch. 19.4 - Treatment of an aldehyde or ketone with cyanide...Ch. 19.4 - p-Nitrobenzaldehyde is more reactive toward...Ch. 19.5 - Prob. 7PCh. 19.5 - The oxygen in water is primarily (99.8) 16O, but...Ch. 19.6 - Prob. 9PCh. 19.8 - Show the products you would obtain by...
Ch. 19.8 - Prob. 11PCh. 19.8 - Prob. 12PCh. 19.9 - Prob. 13PCh. 19.10 - Prob. 14PCh. 19.10 - Prob. 15PCh. 19.11 - What carbonyl compound and what phosphorus ylide...Ch. 19.11 - -Carotene, a yellow food-coloring agent and...Ch. 19.12 - Prob. 18PCh. 19.12 - Prob. 19PCh. 19.13 - Prob. 20PCh. 19.13 - Treatment of 2-cyclohexenone with HCN/KCN yields a...Ch. 19.13 - How might conjugate addition reactions of lithium...Ch. 19.14 - How might you use IR spectroscopy to determine...Ch. 19.14 - Prob. 24PCh. 19.14 - Prob. 25PCh. 19.14 - Prob. 26PCh. 19.SE - Each of the following substances can be prepared...Ch. 19.SE - Prob. 28VCCh. 19.SE - Prob. 29VCCh. 19.SE - Prob. 30MPCh. 19.SE - Prob. 31MPCh. 19.SE - Prob. 32MPCh. 19.SE - Prob. 33MPCh. 19.SE - Prob. 34MPCh. 19.SE - Prob. 35MPCh. 19.SE - It is not uncommon for organic chemists to prepare...Ch. 19.SE - Prob. 37MPCh. 19.SE - Prob. 38MPCh. 19.SE - Prob. 39MPCh. 19.SE - Prob. 40MPCh. 19.SE - Aldehydes and ketones react with thiols to yield...Ch. 19.SE - Prob. 42MPCh. 19.SE - When cyclohexanone is heated in the presence of a...Ch. 19.SE - Prob. 44MPCh. 19.SE - The Meerwein-Ponndorf-Verley reaction involves...Ch. 19.SE - Propose a mechanism to account for the formation...Ch. 19.SE - Prob. 47MPCh. 19.SE - Prob. 48MPCh. 19.SE - Treatment of an , -unsaturated ketone with basic...Ch. 19.SE - Prob. 50MPCh. 19.SE - Prob. 51MPCh. 19.SE - Prob. 52MPCh. 19.SE - Prob. 53MPCh. 19.SE - Prob. 54APCh. 19.SE - Draw and name the seven aldehydes and ketones with...Ch. 19.SE - Give IUPAC names for the following compounds:Ch. 19.SE - Draw structures of compounds that fit the...Ch. 19.SE - Predict the products of the reaction of (1)...Ch. 19.SE - Show how you might use a Wittig reaction to...Ch. 19.SE - How would you use a Grignard reaction on an...Ch. 19.SE - Prob. 61APCh. 19.SE - Prob. 62APCh. 19.SE - How would you synthesize the following substances...Ch. 19.SE - Carvone is the major constituent of spearmint oil....Ch. 19.SE - How would you synthesize the following compounds...Ch. 19.SE - At what position would you expect to observe IR...Ch. 19.SE - Acidcatalyzed dehydration of...Ch. 19.SE - Choose the structure that best fits the IR...Ch. 19.SE - Propose structures for molecules that meet the...Ch. 19.SE - Prob. 70APCh. 19.SE - Prob. 71APCh. 19.SE - When 4hydroxybutanal is treated with methanol in...Ch. 19.SE - Prob. 73APCh. 19.SE - Prob. 74APCh. 19.SE - Prob. 75APCh. 19.SE - Prob. 76APCh. 19.SE - Prob. 77APCh. 19.SE - Tamoxifen is a drug used in the treatment of...Ch. 19.SE - Compound A, MW 86, shows an IR absorption at 1730...Ch. 19.SE - Compound B is isomeric with A (Problem 19-79) and...Ch. 19.SE - The 1HNMR spectrum shown is that of a compound...Ch. 19.SE - Prob. 82APCh. 19.SE - Propose structures for ketones or aldehydes that...Ch. 19.SE - Prob. 84APCh. 19.SE - Prob. 85APCh. 19.SE - The proton and carbon NMR spectra for each of...Ch. 19.SE - The proton NMR spectrum for a compound with...
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- Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardPls explain tooarrow_forwardDraw the structure of a compound with the formula C5H10O2 (along with the reasons of choosing it) which, upon analysis, gave key peaks in an infrared spectrum at 3450 cm-1 and 1713 cm-1, as well as the following 1H-NMR spectrum.arrow_forward
- Treatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 20.arrow_forward2 The IR and 1H-NMR spectra of a compound with molecular formula C4H7ClO2 are shown below. Your objective as a group is to propose a structure for this compound, explaining how you reach your decision. Using all the information you have been given, in a post with others in your group share your initial ideas about the possible structure of the compound. Then use comments to interact with the other students in the group and propose a final answer to the problem. In the comment phase, you should comment on the postings of at least two other students.arrow_forwardAs reaction of (CH3)2CO with LIC≡CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600−3200, 3303, 2938, and 2120 cm−1. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?arrow_forward
- Compounds A, B, and C are isomers with the formula C5H11Br. Their broadband proton-decoupled 13C NMR spectra are given below. Information from the DEPT 13C NMR spectra is given near each peak. Give structures for A and B. (Note: part 2 will be posted).arrow_forwardWhat is the structure of the compound which gives rise to this data? Explain your reasoning. NMR SPECTRUM C7H80arrow_forwardSuggest structures given the 1H NMR spectra and formulas for each of the compounds below. C10H14arrow_forward
- The two isomeric compounds with the formula C3H5ClO2 have NMR spectra shown in 4a and 4b below. The downfield protons appearing in the NMR spectra at about 12.1 and 11.5 ppm, respectively, are shown as insets. Determine the structure of the two isomersarrow_forwardA compound of molecular formula C5H12O2 compound has strong infrared absorption at 3300 to 3400 cm-1. Its 1H-NMR spectrum has three singlets at δ 0.9, 3.45, and 3.2 ppm; relative integrals 3:2:1. The 13C-NMR spectrum shows three signals all at higher field than δ 100 ppm. Which of the following compounds best fits this data? a. 2,2-Dimethyl-1,3-propanediol b. 1,3-Dimethoxypropane c.2,4-Pentanediol d. 1,5-Pentanediolarrow_forwardPART 2: Compounds A, B, and C are isomers with the formula C5H11Br. Their broadband proton-decoupled 13C NMR spectra are given below. Information from the DEPT 13C NMR spectra is given near each peak. Give structure for C.arrow_forward
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