Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 16, Problem 69P
How many signals would the product of the following reaction show in
- a. its 1H NMR spectrum?
- b. its 13C NMR spectrum?
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What would be different in the 1H NMR spectra of a mono and disubstituted azulene?How many signals would you expect in the 13C NMR of a mono and disubstituted azulene?
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a. its 1H NMR spectrum? b. its 13C NMR spectrum?
How can you distinguish the following compounds using:a. their infrared spectra? b. their 1H NMR spectra?
Chapter 16 Solutions
Organic Chemistry (8th Edition)
Ch. 16.1 - Give two names for each of the following:Ch. 16.1 - Prob. 2PCh. 16.1 - Name the following:Ch. 16.2 - Prob. 4PCh. 16.4 - What products are formed when the following...Ch. 16.4 - We saw on the previous page that...Ch. 16.4 - a. How many stereoisomers are obtained from the...Ch. 16.4 - Prob. 9PCh. 16.4 - Write the mechanism for the reaction of acetyl...Ch. 16.4 - Prob. 11P
Ch. 16.4 - Show how the following compounds can be...Ch. 16.4 - Prob. 13PCh. 16.4 - Prob. 14PCh. 16.4 - In the mechanism for cyanohydrin formation, why is...Ch. 16.4 - Prob. 16PCh. 16.4 - Prob. 17PCh. 16.4 - Show two ways to convert an alkyl halide into a...Ch. 16.5 - Prob. 20PCh. 16.5 - Prob. 21PCh. 16.5 - Prob. 22PCh. 16.5 - Prob. 23PCh. 16.6 - Prob. 24PCh. 16.7 - What reducing agents should be used to obtain the...Ch. 16.7 - Prob. 26PCh. 16.8 - Prob. 27PCh. 16.8 - Prob. 28PCh. 16.8 - Prob. 29PCh. 16.8 - The pKa of protonated acetone is about 7.5. and...Ch. 16.8 - Prob. 31PCh. 16.8 - Prob. 32PCh. 16.8 - Prob. 33PCh. 16.8 - Excess ammonia must be used when a primary amine...Ch. 16.8 - The compounds commonly known as amino acids are...Ch. 16.9 - Hydration of an aldehyde is also catalyzed by...Ch. 16.9 - Which ketone forms the most hydrate in an aqueous...Ch. 16.9 - When trichloroacetaldehyde is dissolved in water,...Ch. 16.9 - Which of the following are a. hermiacetals? b....Ch. 16.9 - Prob. 40PCh. 16.9 - Explain why an acetal can be isolated but most...Ch. 16.10 - Prob. 42PCh. 16.10 - Prob. 43PCh. 16.10 - What products would be formed from the proceedings...Ch. 16.10 - a. In a six-step synthesis, what is the yield of...Ch. 16.10 - Show how each of the following compounds could be...Ch. 16.12 - Prob. 47PCh. 16.13 - Prob. 49PCh. 16.14 - Prob. 50PCh. 16.15 - Prob. 51PCh. 16.16 - Prob. 52PCh. 16 - Draw the structure for each of the following: a....Ch. 16 - Prob. 54PCh. 16 - Prob. 55PCh. 16 - Prob. 56PCh. 16 - a. Show the reagents required to form the primary...Ch. 16 - Prob. 58PCh. 16 - Prob. 59PCh. 16 - Using cyclohexanone as the starting material,...Ch. 16 - Propose a mechanism for each of the following...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Fill in the boxes:Ch. 16 - Prob. 64PCh. 16 - Identify A through O:Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - How many signals would the product of the...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Prob. 73PCh. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - Prob. 78PCh. 16 - Draw structure for A-D for each of the following:Ch. 16 - Prob. 80PCh. 16 - a. Propose a mechanism for the following reaction:...Ch. 16 - Prob. 82PCh. 16 - A compound gives the following IR spectrum. Upon...Ch. 16 - How can be following compounds be prepared from...Ch. 16 - Prob. 85PCh. 16 - Prob. 86PCh. 16 - Prob. 87PCh. 16 - In the presence of an acid catalyst, acetaldehyde...Ch. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - Prob. 91PCh. 16 - A compound reacts with methylmagnesium bromide...Ch. 16 - Show how each of the following compounds can be...Ch. 16 - Prob. 94PCh. 16 - The pKa values of the carboxylic acid groups of...Ch. 16 - The Baylis-Hillman reaction is a DABCO...Ch. 16 - Prob. 97PCh. 16 - Prob. 98P
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- A B. C. H. CH Br HC-C-CH CHy CH3-C-CH H-C-CH,CH, CH CH, Which of the following compounds give four major peaks in their 1H NMR spectra? OA and B. Band C. A and C. O All of themarrow_forwardUsing 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_forward3. Nuclear Magnetic Resonance Spectroscopy a. Draw the 'H NMR spectrum for the following compound. CIarrow_forward
- 5. How many signals would you expect each of the following molecules to have in its 'H NMR spectrum? Label the structure (a, b, etc...) to correlate protons with the signals in the ¹H NMR spectrums. In which regions of the spectrum would you expect to see each signal? How many hydrogen atoms will each signal integrate for? H or OMe HO Vanillin 4-hydroxy-3-methoxybenzaldehyde HO OH OMe Vanillyl Alcohol 4-hydroxy-3-methoxybenzyl alcoholarrow_forwardQUESTION 3 Briefly explain how you might distinguish between the following substances by comparing their 1H NMR spectra. a. and Compound I Compound II b. Propanal acetonearrow_forward3.How many sets of equivalent protons are there in hexane? a. 2 b. 3 c. 6 d. 7 4. What is the splitting of the signal in the 'H NMR spectrum for the methyl protons of 1-bromo- 2-methylpropane? a. singlet b. doublet c. triplet d. nonet 5. Which C,H,Br compound gives a doublet at approximately 3.3 ppm in the 'H NMR spectrum? 1 b. 2 a. ⠀ c. 3 d. 4 Br H₂C-O-CH₂-CH₂-C-H a. i b. ii c. iii d. iv 2 iv Br 6. Which of the protons in the following molecule appear furthest downfield in the 'H NMR spectrum? Br Brarrow_forward
- Construct a structure of the given 1H NMR data signals.A. C5H12O 0.91 δ (3H, triplet) 1.19 δ (6H, singlet) 1.50 δ (2H, quartet) 2.24 δ (1H, singlet) B. C4H10O 0.90 δ (6H, doublet) 1.76 δ (1H, multiplet) 3.38 δ (2H, doublet) 3.92 δ (1H, singlet) C. C5H10O 1.09 δ (6H, doublet) 2.12 δ (3H, singlet) 2.58 δ (1H, septet)arrow_forward2. The following synthesis was planned. The 'H NMR spectrum of the final product was run and is presented below. Was the synthesis successful? If not, what is the actual product and why? sos H2N' 10 로 1H 2H 2H 8 1. NaNO2 HCI (aq.) 2H 2H 6 2. H 1H 1H PPM 1H OH 1H HO 2arrow_forward1. How many proton signals would be seen in the 'H NMR for the following compounds? 6pt Br Br а. d. f. #3 aiarrow_forward
- What product did you obtain from the competitive nitration of methyl benzoate? a. Which particular IR absorptions led you to this conclusion? b. How can the NMR signals in the aromatic region be used to confirm the identity of your product?arrow_forwardWhich compound gives the following 1H NMR spectrum? A. aldehyde B. allyl ether C. ketone D. anisolearrow_forward1) Which of the following compounds would have the following peaks on a proton NMR spectrum. a. 2-ethylbenzoic acid b. 4ethylbenzoic acid triplet at 1.75 ppm (3H) quartet at 2.25 ppm (2H) Split Quartet at 7.25 ppm(4H) Singlet at 11.00 ppm (1H) c. 3-ethylbenzoic acid d 3-phenylpropanoic acid.arrow_forward
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NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY