Get Ready for Organic Chemistry
Get Ready for Organic Chemistry
2nd Edition
ISBN: 9780321774125
Author: KARTY, Joel
Publisher: PEARSON
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Chapter 7, Problem 7.42P
Interpretation Introduction

Interpretation:

It is to be explained why the equilibrium percentage of the first given molecule in its keto form is lower than that of the second given molecule, referring to Table 7-1.

Concept introduction:

In aqueous basic or acidic conditions, ketones and aldehydes exist in rapid equilibrium with a rearranged form called enol form. As a ketone or aldehyde, the species is called the keto form. In the enol form, the species has a carbon atom that is simultaneously a part of a C = C bond, which is a characteristic of alkenes, and is bonded to OH, which is a characteristic of alcohol. These two forms are always in equilibrium with each other, and this is called keto-enol tautomerization. For cyclic aldehydes and ketones, the percentage of keto form increases as the ring size increases. This is because the angle strain increases in small cyclic rings. The bond angle for a sp2 hybridized carbon atom is larger than it is for a sp3 hybridized carbon atom.

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Part V. Label ad match the carbons in compounds Jane and Diane w/ the corresponding peak no. in the Spectra (Note: use the given peak no. To label the carbons, other peak no are intentionally omitted) 7 4 2 -0.13 -0.12 -0.11 -0.10 -0.08 8 CI Jane 1 -0.09 5 210 200 190 180 170 160 150 140 130 120 110 100 -8 90 f1 (ppm) 11 8 172.4 172.0 f1 (ppr HO CI NH Diane 7 3 11 80 80 -80 -R 70 60 60 2 5 -8 50 40 8. 170 160 150 140 130 120 110 100 90 -0 80 70 20 f1 (ppm) 15 30 -20 20 -60 60 -0.07 -0.06 -0.05 -0.04 -0.03 -0.02 -0.01 -0.00 -0.01 10 -0.17 16 15 56 16 -0.16 -0.15 -0.14 -0.13 -0.12 -0.11 -0.10 -0.09 -0.08 -0.07 -0.06 -0.05 -0.04 17.8 17.6 17.4 17.2 17.0 f1 (ppm) -0.03 -0.02 550 106 40 30 20 20 -0.01 -0.00 F-0.01 10 0

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