Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 5, Problem 3LGP
Interpretation Introduction

Interpretation:

All the chiral centers in cortisone are to be identified and the appropriate (R) or (S) designation for the configuration of each chirality center in it is to be identified.

Concept introduction:

Each center is analyzed separately if the compound contains more than one chirality center.

The designation of each carbon is determined by using the numbers.

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(11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B Bond A Bond C a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest Bond Strongest Bond b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. c. (5pts) Use principles discussed in lecture, supported by relevant structures, to succinctly explain the why your part b (i) radical is more stable than your part b(ii) radical. Written explanation can be no more than one-two succinct sentence(s)!
. 3°C with TH 12. (10pts total) Provide the major product for each reaction depicted below. If no reaction occurs write NR. Assume heat dissipation is carefully controlled in the fluorine reaction. 3H 24 total (30) 24 21 2h • 6H total ● 8H total 34 래 Br2 hv major product will be most Substituted 12 hv Br NR I too weak of a participate in P-1 F₂ hv Statistically most favored product will be major = most subst = thermo favored hydrogen atom abstractor to LL F
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Chapter 5 Solutions

Organic Chemistry

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