Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 14.5, Problem 6P
Assign the chemical shifts
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Sketch the 1H NMR spectra of the following compounds.
Assign the chemical shifts δ 1.1, δ 1.7, δ 2.0, and δ 2.3 to the appropriate protons of 2-pentanone.
The 1H-NMR spectrum of compound B,C7H14O , consists of the following signals: δ 0.9 (t, 6H), 1.6 (sextet, 4H), and 2.4 (t, 4H).
Draw the structural formula of compound B.
Chapter 14 Solutions
Organic Chemistry - Standalone book
Ch. 14.3 - Prob. 1PCh. 14.3 - Prob. 2PCh. 14.4 - The 1H NMR signal for bromoform (CHBr3) appears at...Ch. 14.5 - identify the most shielded and least shielded...Ch. 14.5 - (a) Assign the chemical shifts 1.6, 2.2, and 4.8...Ch. 14.5 - Assign the chemical shifts 1.1, 1.7, 2.0, and 2.3...Ch. 14.5 - Assign the chemical shifts 1.6, 4.0, 7.5, 8.2, and...Ch. 14.6 - The 300-MHz 1H NMR spectrum of 1,4-dimethylbenzene...Ch. 14.6 - Prob. 9PCh. 14.6 - How many signals would you expect to find in the...
Ch. 14.7 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.8 - Describe the appearance of the 1H NMR spectrum of...Ch. 14.11 - Prob. 13PCh. 14.11 - Prob. 14PCh. 14.12 - Hydrogen bonding between the oxygen of dimethyl...Ch. 14.14 - Prob. 16PCh. 14.15 - The 13C NMR spectrum of 1-bromo-3-chloropropane...Ch. 14.15 - Consider carbons x, y, and z in p-methylanisole....Ch. 14.15 - Prob. 19PCh. 14.16 - To which of the compounds of Problem 14.16 does...Ch. 14.18 - DEPT spectra for a compound with the formula...Ch. 14.20 - Vibrational frequencies are sensitive to isotopic...Ch. 14.21 - Prob. 23PCh. 14.22 - Prob. 24PCh. 14.23 - Prob. 25PCh. 14.23 - Which one of the C5H8 isomers shown has its max at...Ch. 14.24 - Knowing what to look for with respect to isotopic...Ch. 14.24 - The base peak appears at m/z105 for one of the...Ch. 14.24 - Mass spectra of 1-bromo-4-propylbenzene and...Ch. 14.25 - Prob. 30PCh. 14 - Each of the following compounds is characterized...Ch. 14 - Deduce the structure of each of the following...Ch. 14 - From among the isomeric compounds of molecular...Ch. 14 - The H1NMR spectrum of fluorene has signals at 3.8...Ch. 14 - Prob. 35PCh. 14 - H1NMR spectra of four isomeric alcohols with...Ch. 14 - Prob. 37PCh. 14 - We noted in Section 14.13 that an NMR spectrum is...Ch. 14 - Identify each of the C4H10O isomers on the basis...Ch. 14 - A compound (C3H7ClO2) exhibited three peaks in its...Ch. 14 - Label nonequivalent carbons in the following...Ch. 14 - Compounds A and B are isomers of molecular formula...Ch. 14 - C13 NMR spectra for four isomeric alkyl bromides...Ch. 14 - Prob. 44PCh. 14 - Prob. 45PCh. 14 - Identify the C3H5Br isomers on the basis of the...Ch. 14 - Prob. 47PCh. 14 - A compound (C8H10O) has the IR and H1NMR spectra...Ch. 14 - Deduce the structure of a compound having the...Ch. 14 - Figure 14.53 presents IR, H1NMR, C13NMR and mass...Ch. 14 - H1NMR, C13NMR, IR, and mass spectra are shown for...Ch. 14 - 1H NMR and IR spectra for a compound with the...Ch. 14 - FriedelCraftsalkylation of benzene with...Ch. 14 - Prob. 54DSPCh. 14 - Prob. 55DSPCh. 14 - Prob. 56DSPCh. 14 - Prob. 57DSPCh. 14 - Prob. 58DSP
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- The two compounds 1,2-dibromobenzene and 1 3-dibromobenzene both have the molecular formula C6H4Brz. a)Draw the chemical structures of the two molecules. b)Can these two molecules be distinguished by 1H NMR spectroscopy? Give reasons for your answer and describe the number of proton environments and their splitting for both molecules. Can these two molecules be distinguished by 13C NMR spectroscopy? Give reasons for your answer. Can these two molecules be distinguished by IR spectroscopy? Give reasons for your answer and describe the main IR signals (with frequencies) you expect to see for both molecules. Can these two molecules be distinguished by mass spectrometry? Give reasons for your answer.arrow_forwardDraw the five isomeric alkanes of molecular formula C6H14. Determine how many proton environments there are in each of the isomers.arrow_forwardThe following 1H NMR spectra are for four compounds, each with molecular formula of C6H12O2. Identify the compounds.arrow_forward
- Draw the three isomeric alkanes of molecular formula C5H12. Determine how many proton environments there are in each of the isomers.arrow_forwardAnalyze the 13C-NMR spectrum of C8H9NO given below and draw the structure of the compound.arrow_forwardConsider carbons x, y, and z in p-methylanisole. One has a chemical shift of δ 20, another has δ 55, and the third δ 157. Match the chemical shifts with the appropriate carbons.arrow_forward
- Below is the 13C NMR spectrum of a compound with molecular formula C7H16O, measured in CDCl3. Identify the two carbons that have chemical shifts at δ 36.4 and 33.5 ppmarrow_forwardGiven that Kb for (CH3)3N is 6.3 × 10-5 at 25 °C, what is the value of Ka for (CH3)3NH at 25 °C?arrow_forwardIndicate two basic differences that exist between the spectra of 1H y 13C in NMR.arrow_forward
- Draw the H1 NMR spectra of ethylcyclopropane. Draw the chemical structure and predict the proton splitting and chemical shifts.arrow_forwardThe 1H NMR spectra of two carboxylic acids with molecular formula C3H5O2Cl are shown below. Identify the carboxylic acids. (The “offset” notation means that the farthest-left signal has been moved to the right by the indicated amount to fit on the spectrum; thus, the signal at 9.8 ppm offset by 2.4 ppm has an actual chemical shift of 9.8 + 2.4 = 12.2 ppm.)arrow_forwardCompound 1 has molecular formula C6H12. It shows three signals in the 1H-NMR spectrum, one at 0.96 ppm, one at 2.03 ppm, and one at 5.33 ppm. The relative integrals of these three signals are 3, 2, and 1, respectively. Compound 2 has molecular formula C7H15Br. It shows two signals in the 1H-NMR spectrum, one at 1.08 ppm and one at 1.59 ppm. The relative integrals of these two signals are 3 and 2, respectively. Propose structures for compounds 1 and 2, explaining how you reach your conclusion.arrow_forward
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