Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 12C.10, Problem 25P

Propose a structure for a compound of molecular formula C 7 H 14 O 2 with an IR absorption at 1740 cm 1 and the following 1 H NMR data:

Absorption ppm Relative area singlet 1 .2 9 triplet 1 .3 3 quartet 4 .1 2

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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? b) How many rings are probably in B? How many double bonds are in B? 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?
Propose a structure for a compound of molecular formula C7H14O2 with an IR absorption at 1740 cm−1 and the following 1H NMR data:                                             Absorption ppm Relative area                             singlet         1.2             9                            triplet          1.3             3                            quartet        4.1             2
Propose a structure given the 1H and 13C NMR spectra of the unknown compound. Assign chemical shifts to corresponding hydrogen and carbon atoms Molecular Formula: C5H10O3

Chapter 12C Solutions

Organic Chemistry (6th Edition)

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