ORGANIC CHEMISTRY W/CONNECT
10th Edition
ISBN: 9781307048513
Author: Carey
Publisher: MCG/CREATE
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Chapter 14.24, Problem 29P
Mass spectra of
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1,3-Dibromobutane has the 1H NMR spectrum shown below. Map each hydrogen atom in the molecule of 1,3-dibromobutane with its corresponding peak number.
Analyze the 1H NMR of 2-phenyl-2-propanol. Based on intensities and splitting patterns, it should be possible to assign all of the peaks in this spectrum.
Analyze the 1H NMR of 2-cyclohexyl-2-propanol. In this case, it is not possible to assign all peaks. Indicate which peaks can be assigned to specific H atoms in this compound.
The base peak appears at m/z 105 for one of the following compounds and at m/z 119 for the other two. Match the compounds with the appropriate m/z values for their base peaks.
Chapter 14 Solutions
ORGANIC CHEMISTRY W/CONNECT
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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- Please help me to interpret this spectrum of Methyl-3-nitrobenzoate.arrow_forwardIn the TLC experiment you are give a mixture of benzoic acid C6H5COOH and 2-hydroxy benzoic acid C6H4 ( OH)COOH. Which will have a higher Rf value in a non polar solvent and why?arrow_forwardFor the 1H NMR, assign all peaks. A drawing of the product is available as part of this assignment which labels each of the different types of hydrogen atoms present (a-h). Assign each of the observed peaks in your measured spectrum to one of these letters. For example, "(3H, triplet) at 1.10 ppm is assigned to hydrogens (a)".arrow_forward
- mention more significant peaks. Infrared spectrum of: 2-aminoethanolarrow_forwardAnalyze the 1H NMR of 2-cyclohexyl-2-propanol. In this case, it is not possible to assign all peaks. Indicate which peaks can be assigned to specific H atoms in this compound.arrow_forwardHere are proton NMR data for 1-bromopropane: Ha : triplet (2H) 3.32ppm; Hb : multiplet (2H)1.81ppm; Hc : triplet (3H) 0.93ppm. (Relative integrations shown in parentheses.) a. Through how many bonds can a hydrogen split another hydrogen? b. According to this splitting rule, does Ha split Hc ? c. Is your answer in part a) consistent with the multiplicity listed for peak clusters a and c? d. How many hydrogenssplit Hb ? e. Upon very close inspection of the proton NMR spectrum of 1-bromopropane, you wouldfind that peak cluster b has at least six peaks. Is this consistent with your answer in part d)? f. Speculate as to why any peak cluster with more than four peaks is listed simply as a"multiplet."arrow_forward
- Following are infrared spectra of nonane and 1-hexanol. Assign each compound its correct spectrum.arrow_forwardFollowing are infrared spectra of 2-methyl-1-butanol and tert-butyl methyl ether. Assign each compound its correct spectrum.arrow_forwardHow many peaks would you expect in the 1H NMR spectrum of 1, 4-dimethyl- benzene (para-xylene, or p-xylene)? What ratio of peak areas would you expect on integration of the spectrum? Refer to Table 13-3 for approximate chemical shifts, and sketch what the spectrum would look like. (Remember from Section 2-4 that aromatic rings have two resonance forms.)arrow_forward
- Please help me correct the peak integrations and multiplicities of the H-NMR for 1-Bromo-2-Hexene.arrow_forwardHow close does your spectrum match to the literature spectrum of ethyl 3-coumarincarboxylate? What are the differences in the two spectra, and how do youexplain them?arrow_forward4.Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. 5. Using the peak information listed in the tables for both structures, assign each peak to that portion of the structure that produces the peak in the NMR spectrum.arrow_forward
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