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, Problem 70P

Propose a structure consistent with each set of data.

a. Compound J: molecular ion at 72 ; IR peak at 1710 cm 1 ; 1 H NMR data (ppm) at 1 .0 ( triplet 3 H ) , 2 .1 ( singlet, 3 H ) , and 2.4 ( quartet, 2 H )

b. Compound K: molecular ion at 88 ; IR peak at 3600 3200 cm 1 ; 1 H NMR data (ppm) at 0 .9 ( triplet 3 H ) , 1 .2 ( singlet, 6 H ) , 1.5 ( quartet, 2 H ) , and 1.6 ( singlet, 1 H ) .9 (triplet, 3 H), 1.2 (singlet, 6 H)

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Compound C has a molecular ion in its mass spectrum at 146 and a prominent absorption in its IR spectrum at 1762 cm. C shows the following 'H NMR spectral data: 1.47 (doublet, 3 H), 2.07 (singlet, 6 H), and 6.84 (quartet, 1 H) ppm. What is the structure of C?
Identify the structures of each compound from the given data.
Propose a structure consistent with each set of spectral data: a. C4H8Br2: IR peak at 3000–2850 cm−1; NMR (ppm):   1.87 (singlet, 6 H)    3.86 (singlet, 2 H) b.C3H6Br2: IR peak at 3000–2850 cm−1; NMR (ppm):   2.4 (quintet)  3.5 (triplet) c. C5H10O2: IR peak at 1740 cm−1; NMR (ppm):    1.15 (triplet, 3 H) 2.30 (quartet, 2 H)     1.25 (triplet, 3 H) 4.72 (quartet, 2 H) d.C3H6O: IR peak at 1730 cm−1; NMR (ppm):     1.11 (triplet)      2.46 (multiplet)      9.79 (triplet)

Chapter 12C Solutions

Organic Chemistry (6th Edition)

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