Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 13.14, Problem 13.32P
Sets of spectra are given for two compounds. For each set,
- A. look at each spectrum individually, and list the structural characteristics you can determine from that spectrum.
- B. look at the set of spectra as a group, and propose a tentative structure.
- C. verify that your proposed structure accounts for the major features of each spectrum. The soluton for compound 1 is given after the problem, but go as far as you can before looking at the solution.
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6. Analyze the two IR’s below. One corresponds to 2,3-dimethyl-1-butene, and the other correspondsto 2,3-dimethyl-2-butene.a. Draw the structures of both molecules.b. Match each compound to the correct spectrum.c. Explain how you arrived at your selection. In your explanation you should state at least tworeasons (e.g. peaks that are missing/present, strong vs weak, symmetry vs. asymmetry) andyou should support your reasons with data from the IR spectra.
Match the four structures with the four IR spectra (by putting a proper letter in the box to the right of each spectrum). Use specific IR absorptions for various functional groups to identify the structures. Circle the important peaks in each spectrum that helped you identify the functional group(s) and label the functional group beside it.
PART 2:
Draw the most accurate 'H-NMR spectrum you can for the following molecules. Show all signals,
including an accurate representation of splitting, intensity and position. Assume NO signal overlap (i.e. if
you expect signals have similar chemical shifts, just place them next to each other). Clearly label the
integration value for each signal. Indicate the correlation between each proton (HA, HB, etc) and each
signal (label signals A, B, etc.) by using the standard subscript system that we have been using for other
problems. This entire assignment is to be completed independently.
i)
12.5
ii)
5
2.5
0 ppm
10
7.5
OH
12.5
10
7.5
2.5
0 ppm
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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 3. Look at the two spectra below, one of which is 2-methylcyclohexanol and one of which is 3methylcyclohexene. Which spectrum belongs to which compound? Explain your reasoning. 10- 4000 200 3500 3000 2500 1500 1000 600 Spectrum A 90 20 30 20 10 500 3000 2500 2000 1600 1000 500 Vieters kn1 Spectrum Barrow_forward1. NMR analysis: Draw the full structure of diphenylmethanol. Show all bonds to the hydrogens. Label the different sets of hydrogens (i.e. Hạ. Hp, H1, H2, etc) based on which ones are equivalent and which ones are not. Assign each set of hydrogens with a specific signal on the spectrum. Create a table that summarizes: the chemical shift, integration, multiplicity, proton assignment, and justification of each signal.arrow_forwardCould you answer questions 4 and 5 please, thank you.arrow_forward
- refer to image please please label graph and show all work. CALCULATE R VALUE AND EXPLAIN. will only rate if graph is labelled. label name of structure too.arrow_forwarda. Are any of the spectra that of an alcohol? If so, which? What absorption pattern(s) at what wavelength(s) identifies an alcohol? b. Are any of the spectra that of a compound containing a benzene ring? If so, which? What three absorption patterns at what wavelengths show that a compound has a benzene ring?arrow_forwardWhat type of spectroscopy would be best to differentiate each pair of molecules? If there is more than one type, please list any/both. Do not include X-ray diffraction.arrow_forward
- How many different 'H signals appear for this compound? OA. A. 10 OB. 9 O C. 8 OD. 7 OE.6arrow_forward1. methyl butanoate2. benzaldehyde3. 1-chlorobutane4. 1-chloro-2-methylpropane5. butan-2-one6. propan-2-ol7. propanal For each of the possible listed unknowns above, draw and label its structure. Then, provide a brief description of how you will identify the corresponding proton NMR spectrum for that compound. Be specific.arrow_forwardAcetyleugnol: Match the peaks to the appropriate number on the structure.arrow_forward
- You may draw the structures in either Kekule, condensed, or mixed format initially. In the tables draw them as skeletal structures. Attach the sheet of paper with your DEPT spectra at the end of this packet before turning your packet in.arrow_forward4. Propose a structure (Lewis structure okay) with molecular formula C13H18O2 that is consistent with the ¹H-NMR spectrum below. Place your structure in the box and label each hydrogen atom using the corresponding labels given in the spectrum (a, b, c, etc.). Note that the peak labeled "TMS" at 0 ppm is not part of your proposed structure and should not be included. Hints: the MS of this molecule has major fragment peaks at m/z = 57 and 73; calculate the IHD for the given molecular formula. arbitrary intensity 4. Draw structure and label hydrogen atoms a br s 1H 12 115 11 105 10 95 85 b c d 2H d 2H *** 'ક 6 pom 35 P q 1H e d 2H g d 3H f m 1H h d 6H 05 TMS 35arrow_forwardFor 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_forward
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