Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 15.17, Problem 36P
Explain why the chemical shift of the OH proton of a
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Chapter 15 Solutions
Organic Chemistry
Ch. 15.1 - Prob. 1PCh. 15.1 - Prob. 2PCh. 15.4 - How many signals would you expect to see in the 1H...Ch. 15.4 - Prob. 4PCh. 15.4 - How could you distinguish the 1H NMR spectra of...Ch. 15.4 - Draw an isomer of dichlorocyclopropane that gives...Ch. 15.5 - Prob. 7PCh. 15.5 - Prob. 8PCh. 15.5 - Prob. 9PCh. 15.5 - Where would you expect to find the 1H NMR signal...
Ch. 15.6 - Prob. 11PCh. 15.7 - Prob. 12PCh. 15.7 - Prob. 13PCh. 15.7 - Without referring to Table 14.1, label the proton...Ch. 15.8 - [18]-Annulene shows two signals in its 1H NMR...Ch. 15.9 - How would integration distinguish the 1H NMR...Ch. 15.9 - Which of the following compounds is responsible...Ch. 15.10 - Prob. 19PCh. 15.10 - Explain how the following compounds, each with the...Ch. 15.10 - The 1H NMR spectra of two carboxylic acids with...Ch. 15.11 - Draw a diagram like the one shown in Figure 14.12...Ch. 15.12 - Indicate the number of signals and the...Ch. 15.12 - How can their 1H NMR spectra distinguish the...Ch. 15.12 - Identify each compound from its molecular formula...Ch. 15.12 - Prob. 27PCh. 15.12 - Propose structures that are consistent with the...Ch. 15.12 - Describe the 1H NMR spectrum you would expect for...Ch. 15.13 - Prob. 30PCh. 15.13 - Identify the compound with molecular formula...Ch. 15.14 - Prob. 32PCh. 15.15 - a. For the following compounds, which pairs of...Ch. 15.17 - Explain why the chemical shift of the OH proton of...Ch. 15.17 - Prob. 37PCh. 15.17 - Prob. 38PCh. 15.17 - Prob. 39PCh. 15.20 - Answer the following questions for each compound:...Ch. 15.20 - Prob. 41PCh. 15.20 - How can 1,2-, 1,3-, and 1,4-dinitrobenzene be...Ch. 15.20 - Identify each compound below from its molecular...Ch. 15.22 - Prob. 44PCh. 15.22 - What does cross peak X in Figure 14.34 tell you?Ch. 15 - Prob. 46PCh. 15 - Draw a spitting diagram for the Hb proton and give...Ch. 15 - Label each set of chemically equivalent protons,...Ch. 15 - Match each of the 1H NMR spectra with one of the...Ch. 15 - Determine the ratios of the chemically...Ch. 15 - How can 1H NMR distinguish between the compounds...Ch. 15 - Prob. 52PCh. 15 - The 1H NMR spectra of three isomers with molecular...Ch. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Compound A, with molecular formula C4H9Cl, shows...Ch. 15 - The 1H NMR spectra of three isomers with molecular...Ch. 15 - Would it be better to use 1H NMR or 13C NMR...Ch. 15 - There are four esters with molecular formula...Ch. 15 - An alkyl halide reacts with an alkoxide ion to...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Prob. 64PCh. 15 - How can the signals in the 6.5 to 8.1 ppm region...Ch. 15 - The 1H NMR spectra of two compounds, each with...Ch. 15 - Draw a splitting diagram for the Hb proton if Jbc...Ch. 15 - Sketch the following spectra that would be...Ch. 15 - How can 1H NMR be used to prove that the addition...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Dr. N. M. Arr was called in to help analyze the 1H...Ch. 15 - Calculate the amount of energy (in calories)...Ch. 15 - The following 1H NMR spectra are four compounds,...Ch. 15 - When compound A (C5H12O) is treated with HBr, it...Ch. 15 - Identity each of the following compounds from its...Ch. 15 - Identify each of the following compounds from its...Ch. 15 - Identity the compound with molecular formula...Ch. 15 - Identify the compound with molecular formula C6H14...
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- In the proton NMR spectra of aldehydes and ketones, the protons bonded to carbons adjacent to the carbonyl group typically fall into which of the chemica shift (in ppm) ranges below? 0 1.0-2.0 O 4.0-4.5 0 2.0-3.0 9.0-10.0arrow_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_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_forward
- 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_forwardThis is the spectral data for 4-cyclohexene-cis-1,2-dicarboxylic acid - Can you tell whether you have the cis or trans 4-cyclohexene-1,2-dicarboxylic acid based on the number of signals seen on 13C NMR?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
- Can you please explain the 1H NMR spectra pattern of sulfamic acid?arrow_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_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_forward
- Which region (A or B) will Ethane appear in the NMR spectrum and which region (A or B) will Ethanoic acid (2-carbon carboxylic acid or Acetic acid) appear in the NMR spectrum ?arrow_forwardНА ОН HB 2-indanol ОН -HA 1-indanol - Нв (b) Estimate the ¹H chemical shift for HB of 2-indanol and HA of 1-indanol. Is one more downfield than the other or are they expected to be similar? Explain your answer.arrow_forwardConsider the 'H NMR of benzamide. How many proton signals would you expect to find for this compound? O 1) 0 O 2) 3 3) 2 4) 4 5) 5 6) 1arrow_forward
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