EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 14.17, Problem 37P
Explain why the chemical shift of the OH proton of a
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Chapter 14 Solutions
EBK ORGANIC CHEMISTRY
Ch. 14.1 - Prob. 1PCh. 14.1 - Prob. 2PCh. 14.4 - How many signals would you expect to see in the 1H...Ch. 14.4 - How many signals would you expect to see in the 1H...Ch. 14.4 - How could you distinguish the 1H NMR spectra of...Ch. 14.4 - Draw an isomer of dichlorocyclopropane that gives...Ch. 14.5 - Prob. 7PCh. 14.5 - Prob. 8PCh. 14.5 - Prob. 9PCh. 14.5 - Where would you expect to find the 1H NMR signal...
Ch. 14.6 - Prob. 11PCh. 14.7 - Prob. 12PCh. 14.7 - Prob. 13PCh. 14.7 - Without referring to Table 14.1, label the proton...Ch. 14.8 - [18]-Annulene shows two signals in its 1H NMR...Ch. 14.9 - How would integration distinguish the 1H NMR...Ch. 14.9 - Which of the following compounds is responsible...Ch. 14.10 - Prob. 19PCh. 14.10 - Explain how the following compounds, each with the...Ch. 14.10 - The 1H NMR spectra of two carboxylic acids with...Ch. 14.11 - Draw a diagram like the one shown in Figure 14.12...Ch. 14.12 - Indicate the number of signals and the...Ch. 14.12 - Explain the relative chemical shifts of the...Ch. 14.12 - How can their 1H NMR spectra distinguish the...Ch. 14.12 - Identify each compound from its molecular formula...Ch. 14.12 - Predict the splitting patterns for the signals...Ch. 14.12 - Describe the 1H NMR spectrum you would expect for...Ch. 14.12 - Propose structures that are consistent with the...Ch. 14.13 - Prob. 30PCh. 14.13 - Identify the compound with molecular formula...Ch. 14.14 - Prob. 32PCh. 14.15 - a. For the following compounds, which pairs of...Ch. 14.15 - How would the 1H NMR spectra for the four...Ch. 14.17 - Explain why the chemical shift of the OH proton of...Ch. 14.17 - Prob. 38PCh. 14.17 - Prob. 39PCh. 14.17 - Prob. 40PCh. 14.20 - Answer the following questions for each compound:...Ch. 14.20 - Prob. 42PCh. 14.20 - How can 1,2-, 1,3-, and 1,4-dinitrobenzene be...Ch. 14.20 - Identify each compound below from its molecular...Ch. 14.22 - Prob. 45PCh. 14.22 - What does cross peak X in Figure 14.34 tell you?Ch. 14 - Prob. 47PCh. 14 - Draw a spitting diagram for the Hb proton and give...Ch. 14 - Label each set of chemically equivalent protons,...Ch. 14 - Determine the ratios of the chemically...Ch. 14 - How can 1H NMR distinguish between the compounds...Ch. 14 - Prob. 52PCh. 14 - Match each of the 1H NMR spectra with one of the...Ch. 14 - The 1H NMR spectra of three isomers with molecular...Ch. 14 - Prob. 55PCh. 14 - Prob. 56PCh. 14 - Compound A, with molecular formula C4H9Cl, shows...Ch. 14 - Would it be better to use 1H NMR or 13C NMR...Ch. 14 - There are four esters with molecular formula...Ch. 14 - Identify the compound with molecular formula C6H14...Ch. 14 - An alkyl halide reacts with an alkoxide ion to...Ch. 14 - The 1H NMR spectra of three isomers with molecular...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Prob. 65PCh. 14 - How can the signals in the 6.5 to 8.1 ppm region...Ch. 14 - The 1H NMR spectra of two compounds, each with...Ch. 14 - Draw a splitting diagram for the Hb proton if Jbc...Ch. 14 - Sketch the following spectra that would be...Ch. 14 - How can 1H NMR be used to prove that the addition...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Dr. N. M. Arr was called in to help analyze the 1H...Ch. 14 - Calculate the amount of energy (in calories)...Ch. 14 - The following 1H NMR spectra are four compounds,...Ch. 14 - When compound A (C5H12O) is treated with HBr, it...Ch. 14 - Identity the compound with molecular formula...Ch. 14 - Identity each of the following compounds from its...Ch. 14 - Prob. 78PCh. 14 - Identify each of the following compounds from its...
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- Consider the NMR chemical shift of a methoxy proton (R-O-CH3) and the chemical shift of a R2- N-CH3 proton. Which of the following statements are correct? O Chemical shift of both are around 4, making them indistinguishable in most cases. The chemical shift of the methoxy proton will be higher. The R2-N-CH3 proton chemical shift will be higher. O The chemical shift of both are around 1, making the indistinguishable in most cases.arrow_forwardExplain why the carbonyl carbon of an aldehyde or ketone absorbs farther downeld than the carbonyl carbon of an ester in a 13C NMR spectrum.arrow_forwardThe 1H-NMR spectrum of 1-bromopropane shows signals at 1.03, 1.88, and 3.39 ppm. The 1H-NMR spectrum of 2-bromopropane shows signals at 1.73 and 4.21 ppm. Draw these two molecules and assign the correct chemical shift to each proton environment.arrow_forward
- Using the tables, answer the 2 questions at the bottom.arrow_forwardDraw the structure of N,N-diethylethanolamine and label the unique proton environmentsarrow_forwardFor the 1 H NMR spectrum of acetyl salicylic acid shown below, assign each signal to the proton to which it corresponds (the COOH proton does not appear on this spectrum).arrow_forward
- The 1H NMR spectrum of 2-propen-1-ol is shown here. Indicate the protons in the molecule that are responsible for each of the signals in the spectrum.arrow_forwardSelect all the compounds that exhibits a proton spectrum with only one signal. 2,2-dimethylpropane 1,1-dichloroethane propanone propane cyclopentane 1,2-dichloroethane | benzene | Tetra methyl silane 1,4-dimethylbenzenearrow_forwardExplain why the carbonyl carbon of an aldehyde or ketone absorbs farther downfield than the carbonyl carbon of an ester in a 13C NMR spectrum.arrow_forward
- I need help calculating the NMR chemical shifts for this compound.arrow_forwardNeighboring Effect on Proton Chemical Shifts 1H Chemical Shifts X=0,CI,Br X=N,S H X H X H Alkanes H R 10 -CHO 8 aromatic 6. vinylic ppm 7 4 R-X 3 2 1 R-л R Base Shift Increment Base shift CH2: 1.2 a Cl: Base shift CH: 1.5 -OC(=0)R 3.0 -OR CHз 0.9 OH a Ph: a OH: 2.3 1.4 2.4 CH2 1.2 2.3 -Br 2.2 Ph Calculated: 3.6 -CI -Aryl -C(=0)R -C=C CH 1.5 2.4 Calculated: 5.3 Observed: 3.65 1.4 with some small Observed: 4.8 1.0 variations 1.0 With the same neighboring effect, methine > methylene > methyl 1. - R-T (-C=C, -C=0, -Ph, etc.) < R-X (-OR, halogen, etc.) The effects are additive • The B-effect of EWG also contributesarrow_forwardDetermine which of the following belongs to this ir spectra then complete the nmr analymethyl butanoate benzaldehyde 1-chlorobutane 1-chloro-2-methylpropane butan-2-one propan-2-ol propanalarrow_forward
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