Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 9, Problem 37P
The homologous series of primary
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Which best describes a characteristic of the NMR spectra for amines?
O secondary amine have N-H signals around бH 6.0
O protons on the a carbon are more deshielded than protons on the ẞ carbon
O C13 signals for the a carbon of an aliphatic amine appear around ō 20
O protons on the ẞ carbon absorb around б 1.3
Connections to biology
5. Tyrosine is an important amino acid in Biochemistry. Assign the peaks in the ¹H-NMR to the hydrogens
in the structure of tyrosine by placing a, b, c, and d in the appropriate corresponding boxes. The
hydrogen atoms attached to O and N atoms do not need to be labeled on this spectrum.
b
14
12
10
d
HN
C
NH₂
histidine
PPM
OH
Attached is the 1H NMR spec for phenylethylamine. Draw the structure of the amine on the spectrum, and identify each peak (e.g. a labeled H atom on your structure, TMS, etc.)
Chapter 9 Solutions
Organic Chemistry
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM
9.2 What compound with molecular...Ch. 9 - Prob. 3PPCh. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - Prob. 7PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 9PPCh. 9 - PRACTICE PROBLEM 9.9 Propose a structure for...
Ch. 9 - PRACTICE PROBLEM 9.10
What is the dihedral angle...Ch. 9 - PRACTICE PROBLEM 9.11 Draw the most stable chair...Ch. 9 - Prob. 13PPCh. 9 - Prob. 14PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - Prob. 18PPCh. 9 - Prob. 19PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Given the mass spectrum in Figure 9.44 and the...Ch. 9 - Prob. 22PCh. 9 - 9.23 How many 13C NMR signals would you predict...Ch. 9 - Prob. 24PCh. 9 - 9.25 Propose structures for the compounds G and H...Ch. 9 - Prob. 26PCh. 9 - Prob. 27PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Prob. 30PCh. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 33PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 35PCh. 9 - Ethyl bromide and methoxybenzene (shown below)...Ch. 9 - 9.34 The homologous series of primary amines, ,...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.39 Propose structures for compounds E and F....Ch. 9 - Regarding compound J, C2HxCly, use the 1H NMR and...Ch. 9 - 9.38 When dissolved in , a compound (K) with the...Ch. 9 - Compound T (C5H8O) has a strong IR absorption band...Ch. 9 - Deduce the structure of the compound that gives...Ch. 9 - 9.45 Deduce the structure of the compound that...Ch. 9 - The 1H NMR spectrum of a solution of 1,...Ch. 9 - Acetic acid has a mass spectrum showing a...Ch. 9 - The 1H NMR peak for the hydroxyl proton of...Ch. 9 - The 1H NMR study of DMF (N, N-dimethylformamide)...Ch. 9 - 9.48 The mass spectra of many benzene derivatives...Ch. 9 - Prob. 52PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.2 How many 1H NMR signals would the following...Ch. 9 - 9.3. How many 1H NMR signals would...Ch. 9 - 9.4 Which of these C6H14 isomers has the greatest...Ch. 9 - 9.5 How many 13C NMR signals would be given by the...Ch. 9 - Prob. 6QCh. 9 - 9.7 What is the structure of a compound C5H12...
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- Carvone is an unsaturated ketone responsible for the odor of spearmint. If carvone has M+=150 in its mass spectrum and contains three double bonds and one ring, what is its molecular formula?arrow_forwardFor primary amines with no branching on the carbon bearing the nitrogen, the base peak occurs at m/z 30. What cation does this peak represent? How is it formed? Show by drawing contributing structures that this cation is stabilized by resonance.arrow_forward5. Tyrosine is an important amino acid in Biochemistry. Assign the peaks in the 'H-NMR to the hydrogens in the structure of tyrosine by placing a, b, c, and d in the appropriate corresponding boxes. The hydrogen atoms attached to O and N atoms do not need to be labeled on this spectrum. с 11 10 16 00 a H. H- H H -*|| NH₂ Tyrosine d -H ppmarrow_forward
- Which one of these four compounds would give a 13C NMR spectrum with only these three peaks, one at 210, one at 40 and one at 20? H3C OB OD 13C NMR delta (8) values C=O of ketones, aldehydes C=O of acids, esters, amides C=C and C=N C-X (where X = halogen, O) base position, alkyl C OC A OA CH3 H3C B CH3 H3C1 220-200 160-180 100-150 40-70 0 - 40 CH3 H₂C D CH3arrow_forwardAccording to the HNMR and structure of the compound, which protons in the structure match with the peaks? (singlet = s, doublet = d, triplet = t, quartet = q, multiplet = m)arrow_forwardThe proton ¹H (Hydrogen) NMR of a compound, C7H7CI, has the following peaks. Which compound below best fits the data? 10 9 HPM-01-022 2H Doublet 8 7 2H Doublet 6 5 ppm 4 3H Singlet 3 2 1 0arrow_forward
- 10. The proton NMR of a compound has the following peaks. Which compound below best fits the data? A OCH₂CH₂Cl NO₂ B OH CH-CH3 CI broad singlet 55.17 (1H) doublet o 1.49 (3H) quartet & 5.00 (1H) doublet o 7.22 (2H) doublet o 7.38 (2H) C CH₂ CH2-OH CH₂ D CH₂-OH CIarrow_forward2. Consider the two ¹H NMR spectra sketched below that correspond to the molecule shown. Assign the peaks in each spectrum to the different sets of equivalent protons in the molecule. Why do the spectra for this molecule look different when measured at different temperatures? IN 84°C M 38°C 3 N 1 ppmarrow_forwardThe mass spectrum of an alcohol (C5H12O) exhibits a base peak at m/z =59. Is the alcohol most likely pentan-1-ol, pentan-2-ol, or pentan-3-ol? Explain.arrow_forward
- у Give the major peak that would be present in the functional group re following compounds: 2800 OH OH 2700 hydovcoad a ing row X Xarrow_forwardWhich of the following molecules matches the given data? (Note: All the molecules have a M+ = m/z 102) C5H10O2 base peak = m/z 43arrow_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_forward
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