Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 9, Problem 34P
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 - PRACTICE PROBLEM 9.3
Using the method of Section...Ch. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 8PPCh. 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. 12PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 14PPCh. 9 - Prob. 15PPCh. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Prob. 19PPCh. 9 - How many 1H NMR signals (not peaks) would you...Ch. 9 - How many 13C NMR signals would you predict for...Ch. 9 - Prob. 22PCh. 9 - Prob. 23PCh. 9 - Prob. 24PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Compound S (C8H16) reacts with one mole of bromine...Ch. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 30PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 32PCh. 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 - 9.36 Propose structures for compounds E and F....Ch. 9 - 9.37 Use the NMR and IR data below to propose a...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 - Prob. 40PCh. 9 - Deduce the structure of the compound that gives...Ch. 9 - Deduce the structure of the compound that gives...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. 49PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...
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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
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