Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 10, Problem 81P
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An alkyl halide reacts with an alkoxide ion to form a compound whose 1H NMR spectrum is shown here. Identify the alkyl halide and the alkoxide ion.
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You are given an unknown compound B with the molecular formula C5H12O and you take an 1H NMR of B (See below). You were told that B formed when A was reacted with a catalytic amount of H2SO4 and an excess of H2O, A formed. An IR spectra of A is below. Identify A and B in the spaces below
Chapter 10 Solutions
Essential Organic Chemistry, Global Edition
Ch. 10.1 - Prob. 1PCh. 10.2 - What would distinguish the mass spectrum of...Ch. 10.2 - Prob. 3PCh. 10.3 - Prob. 5PCh. 10.3 - Suggest possible molecular formulas for a compound...Ch. 10.3 - Prob. 7PCh. 10.4 - Prob. 8PCh. 10.4 - Prob. 9PCh. 10.5 - Prob. 10PCh. 10.5 - Prob. 11P
Ch. 10.6 - Identify the ketone responsible for the mass...Ch. 10.6 - Prob. 13PCh. 10.8 - Prob. 14PCh. 10.8 - Prob. 15PCh. 10.12 - Which will occur at a larger wavenumber: a. a C :...Ch. 10.13 - Which will occur at a larger wavenumber: a. the C...Ch. 10.13 - Prob. 18PCh. 10.13 - Prob. 19PCh. 10.13 - Which will show an O 8 H stretch at a larger...Ch. 10.14 - Prob. 21PCh. 10.14 - Prob. 22PCh. 10.15 - Prob. 23PCh. 10.15 - Prob. 24PCh. 10.17 - Prob. 25PCh. 10.18 - Prob. 26PCh. 10.18 - Prob. 27PCh. 10.19 - Prob. 28PCh. 10.19 - Prob. 29PCh. 10.22 - How many signals would you expect to see in the 1H...Ch. 10.22 - Prob. 31PCh. 10.22 - Prob. 32PCh. 10.23 - Where would you expect to find the 1H NMR signal...Ch. 10.24 - Prob. 34PCh. 10.25 - Prob. 35PCh. 10.25 - Prob. 36PCh. 10.25 - Prob. 37PCh. 10.26 - Prob. 38PCh. 10.26 - Which of the following compounds is responsible...Ch. 10.27 - Prob. 40PCh. 10.27 - Prob. 41PCh. 10.27 - The 1H NMR spectra of two carboxylic acids with...Ch. 10.28 - Prob. 43PCh. 10.28 - Prob. 44PCh. 10.28 - Prob. 45PCh. 10.28 - Describe the 1H NMR spectrum you would expect for...Ch. 10.28 - Identify the compound with molecular formula...Ch. 10.29 - Prob. 48PCh. 10.29 - Prob. 49PCh. 10.29 - Identify the compound with a molecular formula of...Ch. 10 - In the mass spectrum of the following compounds,...Ch. 10 - For each of the following pairs of compounds,...Ch. 10 - Draw the structure of a saturated hydrocarbon that...Ch. 10 - Prob. 54PCh. 10 - Prob. 55PCh. 10 - How could you use UV spectroscopy to distinguish...Ch. 10 - Prob. 57PCh. 10 - Predict the relative intensities of the molecular...Ch. 10 - Prob. 59PCh. 10 - List the following compounds in order from highest...Ch. 10 - How can 1H NMR be used to prove that the addition...Ch. 10 - There are four esters with molecular formula...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - Each of the IR spectra presented here is...Ch. 10 - Prob. 66PCh. 10 - Five compounds are shown for each of the following...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Phenolphthalein is an acidbase indicator. In...Ch. 10 - Which one of the following five compounds produced...Ch. 10 - Prob. 72PCh. 10 - Prob. 73PCh. 10 - Prob. 74PCh. 10 - How could 1H NMR distinguish between the compounds...Ch. 10 - Prob. 76PCh. 10 - Prob. 77PCh. 10 - The 1H NMR spectra of three isomers with molecular...Ch. 10 - The 1H NMR spectra of three isomers with molecular...Ch. 10 - Identify the following compounds. (Relative...Ch. 10 - An alkyl halide reacts with an alkoxide ion to...Ch. 10 - Determine the structure of a compound with...
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- 5. A compound having molecular formula C,H,OS reacts with hydrazine hydrate forming a product C with molecular formula C₁H,N₂S₂. The ¹H-NMR and ¹C-NMR spectra of the product is given below. Identify compounds A and C. Also, assign each NMR peak. Answer as soon as possible within 10 minutes with proper explanation in handwritten form. Don't answer after 11:58 PM Otherwise I will downvote and report !! Thank youarrow_forward5 Considering the NMR data below, which of these structure is correct?arrow_forward9. Compound A is treated with HONO, followed by a reaction with Compound B; the final product obtained is shown below. H NMR spectra for Compounds A and B are provided. (a) Provide structures of Compounds A and B in the boxes below. (b) Label the signals on each spectrum with letters (as outlined on Week 3 Tuesday slide 4), then assign all H NMR signals to specific chemical environments or specific protons on the structures of Compounds A and B. Compound CompoundA HONO Fr Product H NMR Compound A 2H 1H 1H 1H 1H 3H H NMR Compound B 2H 1H 1H 2Harrow_forward
- 2. What is the structure of the compound which gives rise to this spectrum? Explain your reasoning. "H NMR spectrum doublet. 1.04 (6H multiplet. 6 1.95 (IH doublet. 8 3.35 (2H CH.CIarrow_forward2. The compound with the closed formula C4H9Br gives the following 1H NMR data. Write the clear formula of the compound with reasons. 1.0 ppm (triplet, 3 H); 1.7 ppm (dublet, 3H); 1.8 ppm (multiplet, 2H); 4.2 ppm (multiplet, 1H)arrow_forward4. a. The ¹H NMR spectrum of a compound with the molecular formula C3H₁0O₂ is shown below (integral values are given above each set of peaks). Analysis of its ¹3C NMR spectrum shows peaks at 174, 61, 27, 14 and 9 ppm (see the posted lecture notes for June 7 for some guidance on ¹³C NMR spectroscopy). The IR spectrum shows a prominent peak at 1735 cm¹¹ and no peaks with a stretching frequency above 3000 cm³¹. What is the structure of this compound? 3.0 b. Which peak in the NMR spectrum in part a corresponds to a CH₂ group (called a "methylene") bonded to an O atom? a. 1.12 ppm b. 1.25 ppm c. 2.31 ppm e. There are no CH₂ groups bonded to an O atom in this compound. d. 4.12 ppm 1.0 PPMarrow_forward
- Using proton NMR spectra, how could a chemist distinguish between the following two compounds? H. H. СОСН Ph COCH; Ph H. Compound A Compound B The alkene protons in compound A display a larger coupling constant. Compound A and compound B show a different number of signals in the proton spectrum. The alpha alkene proton would be more shifted than the beta alkene proton in compound B Proton NMR spectroscopy cannot be used to distinguish between these compounds. The alkene protons in compound B display a larger coupling constant.arrow_forwardShow the proton and carbon NMR peaks. This can be the NMR graph OR a list of peaks labeled 1,2,3 or a, b, c. Label the 1H NMR spectral data (1,2,3 or a, b, c) and match the peaks to ALL the product molecule's H by labeling them (1,2,3 or a, b, c). Show that you know which 1H-NMR peaks correspond to each hydrogen atoms on your molecule. Label the 13C NMR spectral data (1,2,3 or a, b, c) and match the peaks to ALL the product molecule's C by labeling them (1,2,3 or a, b, c). Show that you know which 13C NMR peaks correspond to each hydrogen atoms on your molecule. - Ph IZ OH MeO Mearrow_forward13. Compound A has molecular formula C8H18. It shows one singlet in the 1H-NMR spectrum. Identify A and explain your reasoning.arrow_forward
- In the presence of excess base and excess halogen, a methyl ketone is converted to a carboxylate ion. The reaction is known as the haloform reaction because one of the products is haloform (chloroform, bromoform, or iodoform). Before spectroscopy became a routine analytical tool, the haloform reaction served as a test for methyl ketones: the formation of iodoform, a bright yellow compound, signaled that a methyl ketone was present. Why do only methyl ketones form a haloform?arrow_forwardTabulate your 1H NMR data of 2-(2-nitrophenyl)acetonitrile. Label each proton on the structure, and list them separately in a table that is similar to the example below. Be sure to include a row for each unique proton. The H NMR spectra for the structure is attached also.arrow_forwardQ4. The following is the 13C NMR spectrum of a highly concentrated solution of dicyclopentadiene obtained in chloroform-d. Despite the high purity of the compound based on ¹H NMR, there is a massive peak observed at 77.2 ppm in this 13C spectrum, which doesn't correspond to any resonances expected for dicyclopentadiene. What is this peak, and why do you not see a corresponding peak for this compound in your ¹H NMR spectrum? 79-751 <-136.22 -132.62 132.27 132.23 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55 50 45 40 35 30arrow_forward
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NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY