EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 17, Problem 51P
The 1H NMR chemical shifts of nitromethane, dinitromethane, and trinitromethane are at δ 6.10, δ 4.33, and δ 7.52. Match each chemical shift with the compound. Explain how chemical shift correlates with pKa.
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Chapter 17 Solutions
EBK ORGANIC CHEMISTRY
Ch. 17.1 - Prob. 1PCh. 17.1 - Prob. 2PCh. 17.1 - Prob. 3PCh. 17.1 - Prob. 4PCh. 17.1 - Rank the compounds in each of the following groups...Ch. 17.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 17.3 - Draw the enol tautomers for each of the following...Ch. 17.3 - Prob. 8PCh. 17.4 - Prob. 9PCh. 17.4 - Prob. 10P
Ch. 17.5 - Show how the following compounds can be prepared...Ch. 17.6 - What compound is formed when a dilute solution of...Ch. 17.7 - Prob. 13PCh. 17.7 - Prob. 14PCh. 17.7 - How many stereoisomers are obtained from each of...Ch. 17.7 - Prob. 16PCh. 17.8 - Prob. 17PCh. 17.9 - Prob. 18PCh. 17.9 - What reagents should be used to prepare the...Ch. 17.10 - Prob. 20PCh. 17.10 - What aldehyde or ketone would be obtained when...Ch. 17.11 - Prob. 22PCh. 17.11 - How could you prepare the following compound using...Ch. 17.12 - Prob. 25PCh. 17.12 - What two carbonyl compound are required for the...Ch. 17.12 - Propose a mechanism for the following reaction:Ch. 17.13 - Draw the products of the following reactions:Ch. 17.13 - Prob. 29PCh. 17.13 - Prob. 30PCh. 17.14 - Prob. 31PCh. 17.15 - Write the mechanism for the reaction of a...Ch. 17.15 - Prob. 33PCh. 17.15 - Prob. 34PCh. 17.15 - Draw the product of the reaction of each of the...Ch. 17.16 - Draw the product obtained by heating each pair of...Ch. 17.16 - What two carbonyl compounds are needed to...Ch. 17.17 - Prob. 38PCh. 17.18 - Prob. 39PCh. 17.18 - Prob. 40PCh. 17.19 - Prob. 41PCh. 17.20 - Prob. 43PCh. 17.21 - Propose a mechanism for the formation of...Ch. 17.21 - Prob. 45PCh. 17.21 - a. If the biosynthesis of palmitic acid were...Ch. 17.21 - Prob. 47PCh. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Number the following compounds in order of...Ch. 17 - The 1H NMR chemical shifts of nitromethane,...Ch. 17 - Prob. 52PCh. 17 - Draw the products of the following reactions: a....Ch. 17 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 17 - Draw the products of the following reaction:Ch. 17 - Prob. 56PCh. 17 - Prob. 57PCh. 17 - In the presence of excess base and excess halogen,...Ch. 17 - Identify A-L. (Hint: A shows three singles in its...Ch. 17 - Using cyclopentanone as the reactant, show the...Ch. 17 - Show how 4-methyl-3-hexanol can be synthesized...Ch. 17 - Show how the following compound can be synthesized...Ch. 17 - Show how the following compounds can be prepared...Ch. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Indicate how each of the following compounds can...Ch. 17 - Prob. 67PCh. 17 - The ketone whose 1H NMR spectrum is shown here was...Ch. 17 - Indicate how the following compounds can be...Ch. 17 - Compound A with molecular formula C6H10 has two...Ch. 17 - Prob. 71PCh. 17 - Draw the products of the following reactions:Ch. 17 - Prob. 73PCh. 17 - a. Show how the amino acid alanine can be...Ch. 17 - Show how the following compounds can be...Ch. 17 - Prob. 76PCh. 17 - Explain why the following bromoketone forms...Ch. 17 - Prob. 78PCh. 17 - A carboxylic arid is formed when an -haloketone...Ch. 17 - An , -unsaturated carbonyl compound can be...Ch. 17 - What carbonyl compounds are required to prepare a...Ch. 17 - Prob. 82PCh. 17 - A Cannizzaro reaction is the reaction of an...Ch. 17 - Propose a mechanism for each of the following...Ch. 17 - The following reaction is known as the benzoni...Ch. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - Prob. 89PCh. 17 - Prob. 90PCh. 17 - Propose a mechanism for the following reaction:Ch. 17 - What reagents are required to convert the reactant...Ch. 17 - Starting with bromocyclohexane, how can each of...Ch. 17 - Describe how the following compounds can be...Ch. 17 - Prob. 4PCh. 17 - Describe three ways to synthesize the following...Ch. 17 - Explain why 92% of 2.4-pentanedione exists as the...Ch. 17 - Describe how the following compound can be...Ch. 17 - Prob. 8PCh. 17 - Prob. 9PCh. 17 - Prob. 10PCh. 17 - Show how the following compounds can be...
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- Compound A exhibits two signals in its 1H NMR spectrum at 2.64 and 3.69 ppm and the ratio of the absorbing signals is 2:3. Compound B exhibits two signals in its 1 H NMR spectrum at 2.09 and 4.27 ppm and the ratio of the absorbing signals is 3:2. Which compound corresponds to dimethyl succinate and which compound corresponds to ethylene diacetate?arrow_forwardWhich of the following best differentiate the acetanilide from p-nitroacetanilide? p-nitroacetanilide will have 3 H-NMR peaks at around 7.26 ppm while acetanilide will only have 2. acetanilide will have have an N-H IR peak at 3200- 3400 while p-nitroactenilide won't. acetanilide will have 3 H-NMR peaks at around 7.26 ppm while p-nitroacetanilide will only have 2. p-nitroacetanilide will have have an N-H IR peak at 3200-3400 while actenilide won't.arrow_forwardHow would you use IR and ¹H-NMR spectroscopy to distinguish between these two isomeric compounds? For IR, consider the absorption of the carbonyl group. For ¹H-NMR, consider the number of signals observed. Select the IR frequency and number of NMR signals that is diagnostic for either isomer a or isomer b. Isomer A: cyclopentanecarboxamide Isomer B: 6-hydroxyhexanenitrile IR: ¹H-NMR: cm-1. a-4 a-5 b-3 b-4 b-5 b-6 signals a-1680 a-1690 a-1735 a-1810 a-2250 b-1650 b-1690 b-1710 b-2250 24arrow_forward
- Compound X (molecular formula C10H12O) was treated with NH2NH2,−OH to yield compound Y (molecular formula C10H14). Based on the 1H NMR spectra of X and Y given below, what are the structures of X and Y?arrow_forwardFollowing are 1H-NMR spectra for compounds B (C6H12O2) and C (C6H10O). Upon warming in dilute acid, compound B is converted to compound C. Deduce the structural formulas for compounds B and C.arrow_forwardLooking at the NMR & Mass Spectrum, how do you determine the compound is "cyclohexane carboxaldehyde"?arrow_forward
- Aniline and cyclohexylamine are both weak organic bases (see equilibria below). If a researcher needed to separate a mixture of the two compounds, which approach should result in the best separation? NH3* NH2 anilinium ion aniline (pKa = 4.6) NH3* NH2 cyclohexylamonium ion cyclohexylamine (pKa = 10.7) O Dissolve the mixture in ether, then extract once with 150 mL of aqueous 0.1 N NaOH O Dissolve the mixture in ether, then extract with three-50mL aliquots of aqueous 0.1 N NaOH O Dissolve the mixture in ether, then extract once with 150 mL of aqueous 0.1 N HCI O Dissolve the mixture in ether, then extract with three-50mL aliquots of aqueous 0.1 N HCI O Dissolve the mixture in ether, then extract once with 150 mL of saturated aqueous bicarbonate solution O Dissolve the mixture in ether, then extract with three-50 mL aliquots of saturated aqueous bicarbonate solutionarrow_forwardCompound A exhibits two signals in its 1H NMR spectrum at 2.64 and 3.69 ppm, and the ratio of the absorbing signals is 2:3. Compound B exhibits two signals in its 1H NMR spectrum at 2.09 and 4.27 ppm, and the ratio of the absorbing signals is 3:2. Which compound corresponds to dimethyl succinate, and which compound corresponds to ethylene diacetate?arrow_forwardCompound A has molecular formula C7H7X. Its ¹H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C- NMR shows five signals. The mass spectrum of A shows a peak at m/z 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The ¹H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoning Compound B is treated with sodium ethoxide to generate compound C. The ¹H-NMR spectrum of C shows…arrow_forward
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