Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Question
Chapter 9, Problem 14PP
Interpretation Introduction
Interpretation:
The structures for the isomers A, B, and C of the compound with molecular formula, C5H11 Br are to be interpreted from the given DEPT
Concept introduction:
DEPT stands for distortionless enhancement by polarization transfer. DEPT
Presence of the electronegative compounds like halogens or oxygen or sulfur elements will downfield the signal, i.e., the chemical shift will occur at higher δ than the unsubstituted carbons.
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Students have asked these similar questions
2-Methylpentanal and 4-methyl-2-pentanone are constitutional isomers with the
molecular formula C,H,,0. Each shows a molecular ion peak in its mass spectrum at
mlz 100. Spectrum A shows significant peaks at mlz 85, 58, 57, 43, and 42. Spectrum
B shows significant peaks at mlz 71, 58, 57, 43, and 29. Assign each compound its
correct spectrum.
`H
2-Methylpentanal
4-Methyl-2-pentanone
(1) The structural formula of 3-methyl-2-pentenol and 4-amino-4-methyl-2-pentanone,
respectively, are shown below.
HO
CH3
CH3
H₂C
O
53
CH3
NH₂
CH3
(1) Draw a well labeled IR spectrum of each compound showing the peak position and
functional groups.
(ii) Comment, if any, on the similarities or lack of, between the two spectra.
(1) ¹H NMR spectrum of an alcohol (C5H12O) is shown with related integral values
of the each proton peaks. Propose a structure for this alcohol and assign each protons in this
structure.
1H
N->
2
2H
elle
8μ (ppm)
6H
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il
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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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