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 14.24, Problem 29P
Mass spectra of
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A carboxylic acid with the molecular formula C5H10O2 is treated with thionyl chloride to give compound A. Compound A has only one signal in its 1H NMR spectrum. Please figure out this carboxylic acid. You can write out name directly or molecular formula with functional groups (e.g. isopropanol (CH3)3COH). Hint: Only one H NMR signal means all hydrogens are in the same chemical status.
use the attached NMR spectrum to generate the structural formula of the compound .Unknown NMR # 8 was found to be a methyl ketone .Please write down your analysis of each peak and what it corresponds to. After analyzing each peak at whatever ppm, splitting pattern and integration, you should successfully draw the structure of the type alcohol compound
3. What peaks would you expect to find for t-butyl amine vs. diethyl amine vs. n-butyl
amine in the Infrared spectrum?
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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- 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.arrow_forward1. List the integration of all peaks as a ratio. For example, 4-hydroxy-4-methyl-2-pentanone would have a ratio of 1:2:3:6.How does the integration of the peaks correlate to the number of hydrogens present in the molecule? 2. For each peak, draw a partial structure that uses all three pieces of information (chemical shift, integration, splitting patterns). Make sure that you highlight the hydrogen atom or atoms that are responsible for the signal. An example of this is: -CO-CH2-CR2- 3. Based on the chemical shifts, what functional groups are present in your compound? For each, correlate the functional group with the chemical shift of the identifying peak.arrow_forwardBelow is the spectrum for 2-hexanol which has a molecular ion peak of 102. Note that 2-hexanol's molecular ion is very unstable and rapidly undergoes degradation. This is why its molecular ion peak at 102 is almost nonexistent. Give the formula and try to describe the structure that corresponds to the base peak within the spectrum.arrow_forward
- In the box provided, write the IR frequency or range of frequencies that would best distinguish between the two compounds shown. Specify which compound (A or B) will display a band at this frequency in its IR spectrum. Bond O-H (alcohol) O-H (carboxylic acid) N-H Stretching frequency (cm-¹) 3200-3650 2500-3300 3100-3550 2850-3000 3000-3100 C-H (alkane) C-H (alkene) C-H (alkyne) C=C 2100-2250 C=C 1600-1680 C=O (aldehyde/ketone) 1630-1820 C=O (ester) 1735-1800 1700-1725 C=O (carboxylic acid) C-O 1000-1250 A 3300 B OH Intensity Medium, broad Strong, broad Medium Medium Medium to strong Weak to medium Weak Weak to medium Strong Strong Strong Strong (Choose the most prominent frequency. Do not include units in your answer. Use only the frequencies listed above. If there is more than one correct answer, only give one.) Write the letter of the compound, followed by the range of frequencies, separated by a comma. Example. "A,1600-1850". IR frequency or range of frequencies: cm-1 Previous Nextarrow_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_forwardFollowing are infrared spectra of nonane and 1-hexanol. Assign each compound its correct spectrum.arrow_forward
- Here 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_forwardFollowing are infrared spectra of 2-methyl-1-butanol and tert-butyl methyl ether. Assign each compound its correct spectrum.arrow_forwardDraw an expanded structural formula for 3 of the compounds below. How many different resonance peaks (types of hydrogens ) would you expect to find in the H'-NMR spectrum of each of the compounds? Justify your answer, Structure # of peaks splitting pattern of peaks a.acetophenone b.Benzaldehyde c. 2-butanone d.Methyl propanoatearrow_forward
- 1. How many different sets of equivalent aromatic (benzene ring) carbons can be seen in the 13C NMR spectrum of your unknown monosubstituted benzene starting material? A. Are there any peaks for non-aromatic carbons in the 13C NMR spectrum of your unknown monosubstituted benzene starting material (yes or no)? B. If yes for part A, please list the corresponding ppm value(s) for any non-aromatic carbon(s)?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_forwardAcetyleugnol: Match the peaks to the appropriate number on the structure.arrow_forward
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