ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Chapter 16, Problem 16.38SP
(a)
Interpretation Introduction
Interpretation:
The information regarding the molecular formula and IR spectrum for the given compound is given. The structure consistent with the given spectrum and additional information for the given compound is to be stated.
Concept introduction:
NMR data reveals the number and type of hydrogen atoms that are present in a given compound. IR spectra reveal the type of groups that are present in a given compound and MS reveals the structure of a chemical compound. It converts the molecules into respective ions that are studied with the help of electric and magnetic field.
(b)
Interpretation Introduction
Interpretation:
The information regarding the molecular formula and mass spectrum for the given compound is given. The structure consistent with the given spectrum and additional information for the given compound is to be stated.
Concept introduction:
NMR data reveals the number and type of hydrogen atoms that are present in a given compound. IR spectra reveal the type of groups that are present in a given compound and MS reveals the structure of a chemical compound. It converts the molecules into respective ions that are studied with the help of electric and magnetic field.
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Propose possible structures consistent with each set of data. Assume each compound has an sp3 hybridized C – H absorption in its IR spectrum, and that other major IR absorptions above 1500 cm are listed.
a. a compound having a molecular ion at 72 and an absorption in its IR spectrum at 1725 cm−1
b. a compound having a molecular ion at 55 and an absorption in its IR spectrum at ~2250 cm−1
c. a compound having a molecular ion of 74 and an absorption in its IR spectrum at 3600–3200 cm−1
An unknown compound produces an 1H NMR
spectrum with only three signals: 1.8, 2.8, 7.5
(broad) ppm, all singlets that integrate in a 6:3:1
ratio, respectively. The 13C NMR spectrum shows
4 signals. Both spectra are provided below. The
mass spectrum shows a molecular ion region with
the following peaks: m/z 135 (100%), 136 (5.9%),
137 (33%). Determine the number of carbons,
molecular formula, and propose a structure. Assign
all 1H and 13C NMR signals to specific chemical
environments or specific hydrogens in your
structure.
'H NMR Spectrum of Unknown
8
6
PPM
13C NMR Spectrum of Unknown
160
140
80
60
100
PPM
180
120
40
20
Propose possible structures consistent with each set of data. Assume each compound has an sp3 hybridized C—H absorption in its IR spectrum, and that other major IR absorptions above 1500 cm−1 are listed.
a.a compound having a molecular ion at 72 and an absorption in its IR spectrum at 1725 cm−1
b. a compound having a molecular ion at 55 and an absorption in its IR spectrum at −2250 cm−1
c.a compound having a molecular ion at 74 and an absorption in its IR spectrum at 3600−3200 cm−1
Chapter 16 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
Ch. 16.2 - Prob. 16.1PCh. 16.2 - Prob. 16.2PCh. 16.2 - a. Draw the resonance forms of benzene,...Ch. 16.2 - Show the product of the Diels-Alder dimerization...Ch. 16.4 - Prob. 16.5PCh. 16.6 - Make a model of cyclooctatetraene in the tub...Ch. 16.6 - Prob. 16.7PCh. 16.6 - Prob. 16.8PCh. 16.7 - Prob. 16.9PCh. 16.8A - a. Draw the molecular orbitals for the...
Ch. 16.8A - Repeat Problem16-10 for the cyclopentadienyl ions....Ch. 16.8C - Explain why each compound or ion should be...Ch. 16.8C - The following hydrocarbon has an unusually large...Ch. 16.8C - Prob. 16.14PCh. 16.8C - Prob. 16.15PCh. 16.9B - Prob. 16.16PCh. 16.9C - Show which of the nitrogen atoms in purine are...Ch. 16.9C - The proton NMR spectrum of 2-pyridone gives the...Ch. 16.9D - Prob. 16.19PCh. 16.9D - Prob. 16.20PCh. 16.10 - Prob. 16.21PCh. 16.12 - Ciprofloxacin is a member of the fluoroquinolone...Ch. 16.13 - Draw and name all the chlorinated benzenes having...Ch. 16.13 - Name the following compounds:Ch. 16.15 - The UV spectrum of 1-phenylprop-2-en-1-ol shows an...Ch. 16 - Prob. 16.26SPCh. 16 - Name the following compounds:Ch. 16 - Draw and name all the methyl, dimethyl, and...Ch. 16 - Four pairs of compounds are shown. In each pair,...Ch. 16 - One of the following hydrocarbons is much more...Ch. 16 - In Kekuls time cyclohexane was unknown, and there...Ch. 16 - Prob. 16.32SPCh. 16 - Azulene is a deep-blue hydrocarbon with resonance...Ch. 16 - Prob. 16.34SPCh. 16 - Prob. 16.35SPCh. 16 - Prob. 16.36SPCh. 16 - Prob. 16.37SPCh. 16 - Prob. 16.38SPCh. 16 - Prob. 16.39SPCh. 16 - Biphenyl has the following structure. a. Is...Ch. 16 - Anions of hydrocarbons are rare, and dianions of...Ch. 16 - How would you convert the following compounds to...Ch. 16 - Prob. 16.43SPCh. 16 - Prob. 16.44SPCh. 16 - A student found an old bottle labeled thymol on...Ch. 16 - Prob. 16.46SPCh. 16 - Prob. 16.47SPCh. 16 - Prob. 16.48SPCh. 16 - The proton NMR chemical shifts of the hydrogens in...Ch. 16 - Prob. 16.50SPCh. 16 - NMR has been used to probe many molecular...
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