EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Question
Chapter 26, Problem 26.40AP
Interpretation Introduction
Interpretation:
The structure for compound A is to be predicted. The curved arrow mechanism for the preparation of compound A from the compound
Concept introduction:
NMR spectroscopy is a technique used to determine the unique structure of the compounds. It identifies the carbon-hydrogen bonding of an organic compound. A hydrogen atom is called as a proton in the NMR spectroscopy.
The more the shielded proton lesser will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa
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A hydrocarbon, compound B, has molecular formula C6H6, and gave an NMR spectrum with two signals: delta 6.55 pm and delta 3.84 pm with peak ratio of 2:1. When warmed in pyridine for three hr, compound B quantitatively converts to benzene. Mild hydrogenation of B yielded another compound C with mass spectrum of m/z 82. Infrared spectrum showed no double bonds; NMR spectrum showed one broad peak at delta 2.34 ppm. With this information, address the following questions.
a) How many rings are in compound C?
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c) Can you suggest a structure for compounds B and C?
d) In the NMR spectrum of B, the up-field signal was a quintet, and the down field signal was a triplet. How must you account for these splitting patterns?
As a method for the synthesis of cinnamaldehyde (3-phenyl-2-propenal), a chemist treated 3-phenyl-2-propen-1-ol with K2Cr2O7 in sulfuric acid. The product obtained from the reaction gave a signal at δ5 in its 13C NMR spectrum. Alternatively, when the chemist treated 3-phenyl-2-propen-1-ol with PCC in CH2Cl2, the 13C NMR spectrum of the product displayed a signal at δ193.8. (All other signals in the spectra of both compounds appeared at similar chemical shifts.)
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(b) What was the other product?
Treatment of the bicyclic chloride A with lithium in tetrahydrofuran (THF) gave the monocyclic product B, C,H,Li. In
deuterated THF, B exhibited a single proton NMR signal at 6.72 ppm and a single 13 C-NMR signal at about 110 ppm.
Treatment of B with tetraethylammonium chloride gave a white solid in which N(C2H5)4 replaces Li. Draw a structure for
the lithium derivative B.
A
Li/THF
-CI
CgHgLi
(C2H5)4N CI
C9H9N(C2H5)4
B
Draw cations and anions in separate sketchers.
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Chapter 26 Solutions
EBK ORGANIC CHEMISTRY
Ch. 26 - Prob. 26.1PCh. 26 - Prob. 26.2PCh. 26 - Prob. 26.3PCh. 26 - Prob. 26.4PCh. 26 - Prob. 26.5PCh. 26 - Prob. 26.6PCh. 26 - Prob. 26.7PCh. 26 - Prob. 26.8PCh. 26 - Prob. 26.9PCh. 26 - Prob. 26.10P
Ch. 26 - Prob. 26.11PCh. 26 - Prob. 26.12PCh. 26 - Prob. 26.13PCh. 26 - Prob. 26.14PCh. 26 - Prob. 26.15PCh. 26 - Prob. 26.16PCh. 26 - Prob. 26.17PCh. 26 - Prob. 26.18PCh. 26 - Prob. 26.19PCh. 26 - Prob. 26.20PCh. 26 - Prob. 26.21PCh. 26 - Prob. 26.22PCh. 26 - Prob. 26.23PCh. 26 - Prob. 26.24PCh. 26 - Prob. 26.25PCh. 26 - Prob. 26.26APCh. 26 - Prob. 26.27APCh. 26 - Prob. 26.28APCh. 26 - Prob. 26.29APCh. 26 - Prob. 26.30APCh. 26 - Prob. 26.31APCh. 26 - Prob. 26.32APCh. 26 - Prob. 26.33APCh. 26 - Prob. 26.34APCh. 26 - Prob. 26.35APCh. 26 - Prob. 26.36APCh. 26 - Prob. 26.37APCh. 26 - Prob. 26.38APCh. 26 - Prob. 26.39APCh. 26 - Prob. 26.40APCh. 26 - Prob. 26.41APCh. 26 - Prob. 26.42APCh. 26 - Prob. 26.43APCh. 26 - Prob. 26.44APCh. 26 - Prob. 26.45APCh. 26 - Prob. 26.46APCh. 26 - Prob. 26.47APCh. 26 - Prob. 26.48APCh. 26 - Prob. 26.49APCh. 26 - Prob. 26.50APCh. 26 - Prob. 26.51APCh. 26 - Prob. 26.52APCh. 26 - Prob. 26.53AP
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