Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 13, Problem 13.47SP
A compound was isolated as a minor constituent in an extract from garden cress. Its spectra are shown here.
- 1. Look at each spectrum individually, and list the structural characteristics you can determine from that spectrum.
- 2. Look at the set of spectra as a group, and propose a tentative structure.
- 3. Verify that your proposed structure accounts for the major features of each spectrum.
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Consider the following Proton and Carbon NMR spectra for the same compound, and it contains Chlorine. Decide on a structure which is consistent with the spectral data, and 'assign" both spectra as best as you can. "Assign" = draw structure, label (a,b,c etc) and indicate which peaks belong to which type.
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Chapter 13 Solutions
Organic Chemistry (9th Edition)
Ch. 13.5A - In a 300-MHz spectrometer, the protons in...Ch. 13.5B - Prob. 13.2PCh. 13.6 - Determine the number of different kinds of protons...Ch. 13.6 - Prob. 13.4PCh. 13.7 - Draw the integral trace expected for the NMR...Ch. 13.7 - Prob. 13.6PCh. 13.8C - Draw the NMR spectra you would expect for the...Ch. 13.8D - Draw the NMR spectra you expect for the following...Ch. 13.8D - a. Assign protons to the peaks in the NMR spectrum...Ch. 13.8D - Prob. 13.10P
Ch. 13.8D - Two spectra are shown. Propose a structure that...Ch. 13.9 - Prob. 13.12PCh. 13.9 - The spectrum of trans-hex-2-enoic acid follows. a....Ch. 13.9 - Prob. 13.14PCh. 13.9 - Prob. 13.15PCh. 13.10 - Prob. 13.16PCh. 13.10 - If the imaginary replacement of either of two...Ch. 13.10 - Predict the theoretical number of different NMR...Ch. 13.11B - Prob. 13.19PCh. 13.11B - Prob. 13.20PCh. 13.11B - Prob. 13.21PCh. 13.11B - Prob. 13.22PCh. 13.11B - Prob. 13.23PCh. 13.11B - Prob. 13.24PCh. 13.12E - Draw the expected broadband-decoupled 13 C N M R...Ch. 13.12E - a. Show which carbon atoms correspond with which...Ch. 13.12E - Repeat Problem13-25, sketching the...Ch. 13.12F - Prob. 13.28PCh. 13.13 - A bottle of allyl bromide was found to contain a...Ch. 13.13 - A laboratory student was converting cyclohexanol...Ch. 13.14 - Sets of spectra are given for two compounds. For...Ch. 13 - An unknown compound has the molecular formula C 9...Ch. 13 - Prob. 13.34SPCh. 13 - Predict the approximate chemical shifts of the...Ch. 13 - Prob. 13.36SPCh. 13 - Prob. 13.37SPCh. 13 - Prob. 13.38SPCh. 13 - Prob. 13.39SPCh. 13 - Prob. 13.40SPCh. 13 - For each compound shown below. 1. sketch the 13 C...Ch. 13 - Prob. 13.42SPCh. 13 - Prob. 13.43SPCh. 13 - Prob. 13.44SPCh. 13 - Prob. 13.45SPCh. 13 - Prob. 13.46SPCh. 13 - A compound was isolated as a minor constituent in...Ch. 13 - Prob. 13.48SPCh. 13 - The three isomers of dimethylbenzene are commonly...Ch. 13 - a. Draw all six isomers of formula C 4 H 8...Ch. 13 - Prob. 13.51SPCh. 13 - Hexamethylbenzene undergoes free-radical...Ch. 13 - Each of these four structures has molecular...Ch. 13 - Prob. 13.54SPCh. 13 - Phenyl Grignard reagent adds to 2-methylpropanal...Ch. 13 - Prob. 13.56SP
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- Determine the structure of this molecule using the NMR. Please draw the structure and explain how you got it. Thank you for your help!arrow_forward1. Draw two constitutional isomers of the formula C6H11B1. Explain how you would differentiate those molecules using either spectroscopy or spectrometry. You only need to differentiate them using one example.arrow_forwardDetermine the compound (name or structure) from the data. Explain features from each data Molecular formula: C3H8O -Use molecular formula to determine IHD -IR: Identify the presence/absence of five key functional groups -NMR: Analyze this last. Consider multiplicity and peak area to confirm compound -Structure?arrow_forward
- For each of the ten spectra you should determine which peaks are the most important for identification purposes, what their wavenumber values are, and what specific bonds and/or functional groups they indicate. Record those in the spaces under each spectrum. You don’t have to use each space. Then, from the list of possible compounds, identify what compound is responsible for each spectrum. Realize that these are all of real samples and there may be impurities present that cause weak peaks which would not normally be caused by the compound, such as the one at 3450 cm-1 in Spectrum 1.arrow_forwardORGANIC CHEMISTRY PLEASE EXPLAIN, SEE PHOTO: Predict the structure for this unknown. Please provide relevant information regarding each peak and the rationale for how you came to identify each structure. Label any and all peaks. Show all work.arrow_forwardExplain why these are the correct spectra for the molecules. Identify a specific absorption band which identifies each characteristic functional group of the molecule chosen.arrow_forward
- How many different carbon peaks are in the proton-NMR spectrum of tamoxifen (image below)? Note, look at the molecular structure and NMR spectra to determine this number. Discuss why you came to this conclusion and draw pictures/ label to help explain.arrow_forwardFill in the following by identifying the peaks you labeled in your spectrum. Assign the peaks to the functional group vibrations listed. More than one peak (label) may appear for a vibration of a functional group .Functional Group Vibration Aromatic C-H stretching vibration Ketone C O stretching vibration cop bending vibration on monosubstituted aromatic ring (phenyl)..arrow_forwardPredict (draw) the ¹H NMR and 13C NMR spectra for each molecule. Your illustration should include chemical shift, integration, and splitting (where appropriate). Label each signal in your spectrum a, b, c... etc and label the corresponding C/H atoms in each molecule. CIarrow_forward
- 1. How can you distinguish aldehydes, ketones, and carboxylic acids from each other using IR spectra? Explain, using specific examples. 2. How can you distinguish aldehydes, esters, and carboxylic acids using IR spectra? Explain, using specific examples. 3. How can you distinguish an alcohol, a primary amine, and a secondary amine using IR spectra? Explain, using specific examples. 4. How can you distinguish a terminal alkyne and a nitrile using IR spectra? Explain, using specific examples.arrow_forwardBased on the spectra provided, draw the structure. Label each unique carbon and hydrogen with the letters A, B, C… for use in assigning NMR peaks. fill in the data table assigning peaks in each spectrum. You should assign: • All 1H NMR peaks • Significant IR peaks above 1600 cm Example of what the table should include (imagine the structure of ethanol is drawn with the CH3 hydrogens labeled as A, the CH2 hydrogens labeled as B, and the OH hydrogen labeled as C) : hydrogen proton chemical shift integration splitting pattern couples to.. A 1.2 3 triplet B B 3.7 2 quartet A C 2.6 1 singlet -arrow_forwardSelect the bond in each molecule that would be expected to have the strongest IR absorption. Select only one type of bond in each molecule. If there are multiples of one bond type for a molecule, select them all. Do not highlight atoms.arrow_forward
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IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY