Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 10.13, Problem 17P
Which will occur at a larger wavenumber:
- a. the C 8 O stretch of phenol or the C 8 O stretch of cyclohexanol?
- b. the C 9 O stretch of a
ketone or the C 9 O stretch of an amide? - c. The C 8 N stretch of cyclohexylamine or the C 8 N stretch aniline?
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Which occurs at a larger wavenumber:
a. the C - O stretch of phenol or the C - O stretch of cyclohexanol? b. the C - O stretch of a ketone or the C - O stretch of an amide? c. the C - N stretch of cyclohexylamine or the C - N stretch of aniline?
Use resonance theory to explain why the carbonyl (C=O) stretch for prop-2-enal (CH2=CH-CHO) occurs at a lower wavenumber than the carbonyl (C=O) stretch for propanal (CH3-CH2-CHO). It will be necessary to draw structures to support your answer.
Complete the table with at least 3 Major NMR shifts. (stilbene)
Chapter 10 Solutions
Essential Organic Chemistry (3rd 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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- a) what bond is present in ketones but not alkanes? b) what is the wavenumber range of the signals that are present in the diagnostic region of all of the ketone IR spectra (but not the alkanes)? c) is the new band strong or weak compared with a C=C or a C≡C stretch?arrow_forwardWhich shows an absorption band at a larger wavenumber: a carbonyl group bonded to an sp3 carbon or a carbonyl group bonded to an sp2 carbon of an alkene?arrow_forwardWhat are the wavenumber values for the following organic functional groups: C=OAldehyde, Ketone, Amide, Carboxylic acid, and Ester? C=C, C=N, C-H, and C-C.arrow_forward
- What are the following values for 2-bromo-cyclohexanone NMR in the attached table?arrow_forward03) Below are presented two 1H NMR spectra. Among the compounds pentan-3-ol, pentan2-ol, pent-3-amine, pent-2-amine, pentan-2-one, which one corresponds to spectrum A and which one to B? Justify based on chemical shifts and multiplicity of spectra signalsarrow_forwardThe hormone cortisone contains C, H, and O, and shows a molecular ion at M+=360.1937 by high-resolution mass spectrometry. What is the molecular formula of cortisone? (The degree of unsaturation for cortisone is 8.)arrow_forward
- Is the following IR spectra a acetone, benzaldehyde, or dibenzalacetone?arrow_forwardWhich occurs at a larger wavenumber: 1. a C=C stretch or a C=C stretch? 3. a C-N stretch or a C=N stretch? 2. a C-H stretch or a C-H bend? 4. a C=O stretch or a C-O stretch?arrow_forward6 I have to answer the following questions relating to the attached HNMR spectrum. a. Match the hydrogens in dibenzalacetone to the signals in the spectrum. b. Does this sample also contain any benzaldehyde? c. Does this sample also contain any other impurities?arrow_forward
- Directly label the bonds/functional groups on the IR spectrum. Label all major peaksarrow_forwardConsider isomeric alcohols A and B and mass spectra [1] and [2]. (a) Label the molecular ion and base peak in each spectrum. (b) Use thefragmentation patterns to determine which mass spectrum correspondsto isomer A and which corresponds to isomer B.arrow_forwardExamine the IR spectrum in Photo 1. Record the wavenumber for each relevant peak in Data Table 1. Record the bond represented by each relevant peak. Identify the functional groups associated with each bond and record it. Circle the structure(s) on Photo 2 that match the data.arrow_forward
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