Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 13.12E, Problem 13.26P
- a. Show which carbon atoms correspond with which peaks in the 13 C N M R spectrum of butan-2-one (Figure 13-45).
- b. Draw the proton NMR spectrum you would expect lor butan-2-one. How well do the proton chemical shifts predict the carbon chemical shifts using the “15 to 20 times as large” rule of thumb?
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Students have asked these similar questions
a. Rank the indicated protons in increasing order of chemical shift. Fill in the boxes with
the correspondants letters to the indicated hydrogens.
b. Explain your choice of chemical shifts order for protons He and Hd.
Hc
Ha
Ha
He
< SH
< δΗ
8 H
< SH
Hb
< SH
For the following 9 compounds (most of which were the ones used in this
lab), tell me what peaks you would expect to see in the 'H-NMR spectrum of
those compounds. I have provided table for you to fill out with approximate
chemical shift (ppm units), peak multiplicity_(singlet, doublet, etc.) and
integration of the signal (how many protons would give that signal). No IR
data is required. In addition, tell me the number of 13C-NMR signals you
would expect to see [specific 13C shifts are not required]
Predict
1. Which proton has the largest multiplicity? Smallest multiplicity?
Ha
Hd.
Hb
2. Which proton has the largest chemical shift? Smallest chemical shift?
He
Hc
Hf
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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- 'H-NMR exercises A. Number of signals, integration, and multiplicity 1. Determine the number of signals, the integration per signal, and the multiplicity of each signal for the 1H-NMR spectrum of the following molecule B. Chemical Displacement 1. With the chemical shift table determine what type of proton are the protons H., He and He ( >: C. Unknown C,H20 1. Complete the table below, indicating in the corresponding spaces. Sign 2. Using the same structure, place in descending order of chemical shift (highest to lowest) of the protons H., Ho, and He(): ->__ A B C 188 chemical shift 7.2 35 2 C₂H12O Integration PPM 112 76 unfolding Hal 75 3 multiplete ho C-CEC-H₂ Proton Typearrow_forwardHow does H-nmr shift work ? like how do i know which line goes where ?arrow_forwarda. How many signals does this compound have in the 13C NMR spectrum? b. The 13C NMR spectrum for methyl propanoate, CH;CH2COOCH3, is given below. Decide which carbon atoms in the methyl propanoate are for each of the lines in the spectrum. 200 180 160 140 120 100 80 60 40 20 ppm CDS-00-143arrow_forward
- Structure (add letters for labels) 12 ¹H NMR 220 Sketch of ¹H NMR spectrum: H 13C NMR sketch H Assignment Chemical Shift (corresponds (ppm) to label on structure) Chemical Shift (ppm) Chemical Shift (ppm) Integration (# H's per signal) Splitting 0 0arrow_forward14) The intensity of a signal in a ¹H NMR spectrum is determined by A. The number of neighboring C. Number of enantiotopic B. The electronic environment of D. Number of equivalent E. Number of non-equivalent protons.arrow_forward2. Rank Ha, Hb, and Hc in order of increasing chemical shift. Hb Hc H2 H3C CH3 Hd OCH2CH3 Hb Ha На Не а. b.arrow_forward
- Analyze the H1 NMR of the following reaction and label each Hydrogen. Then calculate the chemical shifts for each? Also write multiplicity?arrow_forwardFind the Structural Formula in 13C-NMR Spectra of C4H10O. Compute the IHD, identify the species per peak, and solve the structural formula. A. Computation: B. Analysis/ Interpretation: How many types of C (number of signals and splitting signals)? What types of C (chemical shift)?arrow_forward1. Which proton has the largest multiplicity? Smallest multiplicity? Ha Hd. 2. Which proton has the largest chemical shift? Smallest chemical shift? He Hb Hc N Hf 3. Protons A-E are identified on the spectrum below and correspond to the five unique protons in the molecule shown. (a) Place all the protons on the molecule and categorize them into Ha, Hb, etc. (b) Fill in the table for this molecule (see answer sheet).arrow_forward
- Consider the proton NMR spectrum of styrene and splitting trees for the H* and H protons. SOH2 SOHZ ++++++ OHz SOH2 ++++ H H° C=C 6.78 6.66 5.18 5.66 $28 s.18 10 9 6. 1 8 (ppm) FIGURE 13-31 Proton NMR spectrum of styrene. 85.65 8 6.6 shift of H chemical shift of H = 17 Hz Jah = 17 Hz Je = 1.4 Hz Jo = 11 Hz c=11 Hz Part A Draw a splitting tree, similar to those for H" and H", for proton H in styrene. Drag the appropriate labels to their respective targets. Reset Help 2.3 5.16 85.58 Jac = 21 Joc = OI 1.4 11 Hzarrow_forward7) A molecule has a chemical formula of C6H1202 and produces the spectrum below. Determine its structure. Any labile protons, if they exist, might be present in this 1H NMR spectrum. All signals are singlets. 11 10 HSP-00-610 9 8 7 6 5 ppm 1H 4 -M 3 2H 3H - N 2 6H 1arrow_forwardConstruct a simulated proton-decoupled C NMR spectrum for tert-butyl alcohol. Drag the resonance signal icon to the appropriate chemical shift positions. Then label the box above each resonance signal with the corresponding number of equivalent carbons. (Not all chemical shift bins will be used.) OH 220 200 180 160 140 120 100 80 60 40 8 (ppm) Answer Bank 2C 3C 1C 20arrow_forward
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