Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 13.9, Problem 16P
How could you use 1H NMR to determine the regiochemistry of electrophilic addition to
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This question relates to the1H-NMR spectrum of alkenes.
How many proton environments are there in propene?
How many proton environments are there in trans-2-butene?
What are the multiplicities of each proton environment in trans-2-butene?
What are the multiplicities of each proton environment in propene?
How can 1H NMR be used to prove that the addition of HBr to propene follows the rule that says that the electrophile adds to the sp2 carbon bonded to the most hydrogens?
Addition of m-xylene to the strongly acidic solvent HF/SbF5 at -45°C gives a new species, which shows 1H-NMR resonances at d 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.
Chapter 13 Solutions
Organic Chemistry
Ch. 13.1 - Prob. 1PCh. 13.1 - Prob. 2PCh. 13.2 - Prob. 3PCh. 13.3 - The following 1H NMR peaks were recorded on a...Ch. 13.3 - When the 1Η NMR spectrum of acetone, CH3COCH3, is...Ch. 13.4 - Each of the following compounds has a single 1H...Ch. 13.4 - Identify the different types of protons in the...Ch. 13.5 - How many peaks would you expect in the 1H NMR...Ch. 13.6 - Predict the splitting patterns you would expect...Ch. 13.6 - Draw structures for compounds that meet the...
Ch. 13.6 - The integrated 1H NMR spectrum of a compound of...Ch. 13.7 - Identify the indicated sets of protons as...Ch. 13.7 - How many kinds of electronically nonequivalent...Ch. 13.7 - How many absorptions would you expect (S)-malate,...Ch. 13.8 - 3-Bromo-1-phenyl-1-propene shows a complex NMR...Ch. 13.9 - How could you use 1H NMR to determine the...Ch. 13.11 - Prob. 17PCh. 13.11 - Propose structures for compounds that fit the...Ch. 13.11 - Prob. 19PCh. 13.12 - Prob. 20PCh. 13.12 - Prob. 21PCh. 13.12 - Prob. 22PCh. 13.13 - Prob. 23PCh. 13.SE - Into how many peaks would you expect the 1H NMR...Ch. 13.SE - How many absorptions would you expect the...Ch. 13.SE - Sketch what you might expect the 1H and 13C NMR...Ch. 13.SE - How many electronically nonequivalent kinds of...Ch. 13.SE - Identify the indicated protons in the following...Ch. 13.SE - Prob. 29APCh. 13.SE - Prob. 30APCh. 13.SE - When measured on a spectrometer operating at 200...Ch. 13.SE - Prob. 32APCh. 13.SE - Prob. 33APCh. 13.SE - How many types of nonequivalent protons are...Ch. 13.SE - The following compounds all show a single line in...Ch. 13.SE - Prob. 36APCh. 13.SE - Propose structures for compounds with the...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Predict the splitting pattern for each kind of...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - Identify the indicated sets of protons as...Ch. 13.SE - The acid-catalyzed dehydration of...Ch. 13.SE - How could you use 1H NMR to distinguish between...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Propose structures for the two compounds whose 1H...Ch. 13.SE - Prob. 46APCh. 13.SE - How many absorptions would you expect to observe...Ch. 13.SE - Prob. 48APCh. 13.SE - How could you use 1H and 13C NMR to help...Ch. 13.SE - How could you use 1H NMR, 13C NMR, and IR...Ch. 13.SE - Assign as many resonances as you can to specific...Ch. 13.SE - Assume that you have a compound with the formula...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - The compound whose 1H NMR spectrum is shown has...Ch. 13.SE - Propose structures for compounds that fit the...Ch. 13.SE - Long-range coupling between protons more than two...Ch. 13.SE - The 1H and 13C NMR spectra of compound A, C8H9Br,...Ch. 13.SE - Propose structures for the three compounds whose...Ch. 13.SE - The mass spectrum and 13C NMR spectrum of a...Ch. 13.SE - Compound A, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - Propose a structure for compound C, which has...Ch. 13.SE - Prob. 62GPCh. 13.SE - Propose a structure for compound E, C7H12O2, which...Ch. 13.SE - Compound F, a hydrocarbon with M+=96 in its mass...Ch. 13.SE - 3-Methyl-2-butanol has five signals in its 13C NMR...Ch. 13.SE - A 13C NMR spectrum of commercially available...Ch. 13.SE - Carboxylic acids (RCO2H) react with alcohols (ROH)...Ch. 13.SE - Prob. 68GPCh. 13.SE - The proton NMR spectrum is shown for a compound...Ch. 13.SE - The proton NMR spectrum of a compound with the...Ch. 13.SE - The proton NMR spectrum is shown for a compound...
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- Nitriles, R–=C≡N, undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH3CH2C≡N, if it has IR absorptions from 2500–3100 cm-1 and at 1710 cm-1, and has M+=74?arrow_forwardAcidcatalyzed dehydration of 3hydroxy3phenylcyclohexanone leads to an unsaturated ketone. What possible structures are there for the product? At what position in the ER spectrum would you expect each to absorb? If the actual product has an absorption at 1670 cm-1, what is its structure?arrow_forwardThis question relates to the1H-NMR spectrum of alkenes. What are the multiplicities of each proton environment in trans-2-butene? What are the multiplicities of each proton environment in propene?arrow_forward
- Please explain why if the 13C & 1H NMR spectrum data below is the possible structure of known compound ' 1-(4'-methyl-[1,1'-biphenyl]-4-yl)ethanone'? (Suzuki Cross-Coupling) 1H NMR: 2.41 ppm, 3H, singlet, aromatic -CH3 2.64 ppm, 3H, singlet, ketone, -CH3 7.27-7.29 ppm, 2H,doublet, aromatic -CH 7.53-7.54 ppm, 2H,doublet, aromatic -CH 7.67-7.68 ppm, 2H,doublet, aromatic -CH 8.01-8.03 ppm, 2H,doublet, aromatic -CH 13C NMR 22 ppm, -CH3 attached to the aromatic ring 26 ppm, -CH3 attached to the ketone carbonyl 127 ppm, aromatic -CH 129 ppm, aromatic -CH 130.5 ppm, aromatic -CH 135 ppm, aromatic -CH 137 ppm, aromatic -CH 145 ppm, aromatic -CH 197 ppm, carbonyl carbon of ketone IR: A band at 3040 cm-1 is a stretching frequency of the C-H bond of the alkene. A band at 1672 cm-1 is a stretching frequency of the -C=O bond of ketone (alpha beta unsaturated ketone). A band at 1598 cm-1 is a stretching frequency of the C=C bond of the aromatic ring. A band at 1391 and 1362 cm-1 is a bending…arrow_forwardThis question relates to the1H-NMR spectrum of an alkane and two alkenes. How many proton environments are there in 2-methylbut-2-ene? How many proton environments are there in 1-bromo-4-chlorobutane? How many proton environments are there in trans-2-pentene What are the multiplicities of each proton environment in 2-methylbut-2-ene? What are the multiplicities of each proton environment in 1-bromo-4-chlorobutane? What are the multiplicities of each proton environment in trans-2-pentene?arrow_forwardWhich of the following molecules would have 5 peaks in its 13C NMR spectrum? (Could be multiple) a.) cyclohexane b.) 3-methylpentane c.) 1,3-dimethylcyclobutane d.) methylcyclohexane e.) 2,2-dimethylpentane f.) 1-chloro-2-methylcyclopentanearrow_forward
- How can you use 1H NMR spectroscopy to distinguish between CH2 = C(Br)CO2CH3 and methyl (E)-3-bromopropenoate, BrCH = CHCO2CH3?arrow_forwardChoose the structure corresponding to the given 1H and 13C NMR spectraarrow_forward1. This question relates to the the1H-NMR spectrum of an alkane and two alkenes. a. How many proton environments are there in 2-methylbut-2-ene? b. How many proton environments are there in 1-bromo-4-chlorobutane? c. How many proton environments are there in trans-2-pentene d. What are the multiplicities of each proton environment in 2-methylbut-2-ene? e. What are the multiplicities of each proton environment in 1-bromo-4-chlorobutane? f. What are the multiplicities of each proton environment in trans-2-pentene?arrow_forward
- 4-t-butylcyclohexanone was transformed to cis and trans-4-t-butylcyclohexanol using NaBH4. How can we tell that the trans isomer is prefered from the following NMRs? Make sure to explain why the product distribution occurs in the reaction. (PICTURE that says 1H is the same NMR just zoomed).arrow_forwardCyclohexene has the formula C6H1o and the structure shown in Figure 4-4. When cyclohexene is treated with acid and water it forms Compound A with the formula C6H12O. When Compound A is treated with an oxidizing agent, it forms Compound B with the formula C6H100. IR spectra for Compounds A and B are shown in Figure 4-3. The best structure for A is The best for B isarrow_forwardFully interpret the 1H-NMR spectrum of 4-vinylbenzoic acid providedarrow_forward
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