Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Question
Chapter 6, Problem 6.32AP
Interpretation Introduction
Interpretation:
The structure of the chiral
Concept introduction:
A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. A carbon atom that does not have four nonequivalent atoms or groups attached to it is known as an achiral carbon atom.
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For the cyclohexane structures shown below, draw both chair structures for each and identify which is lower in energy (briefly explain why).
The energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).
I'm confused as to why the chiral centers are the was they are. I understand that the horizontal lines are wedged and vertical are dashed. Wouldn't the first priority be the carboxylic acid, then alcohol, the carbon, and then the hydrogen? The book is saying that one method is to keep two of the straight lines and pick one group to be dashed and one to be wedged. Then switch the last priority group (H) with whatever group you chose to be on the dash. Whatever configuration you get, make it the opposite since you switched groups. And when I use this method I end up getting S when the top one should be R.
Chapter 6 Solutions
Organic Chemistry
Ch. 6 - Prob. 6.1PCh. 6 - Prob. 6.2PCh. 6 - Prob. 6.3PCh. 6 - Prob. 6.4PCh. 6 - Prob. 6.5PCh. 6 - Prob. 6.6PCh. 6 - Prob. 6.7PCh. 6 - Prob. 6.8PCh. 6 - Prob. 6.9PCh. 6 - Prob. 6.10P
Ch. 6 - Prob. 6.11PCh. 6 - Prob. 6.12PCh. 6 - Prob. 6.13PCh. 6 - Prob. 6.14PCh. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Prob. 6.17PCh. 6 - Prob. 6.18PCh. 6 - Prob. 6.19PCh. 6 - Prob. 6.20PCh. 6 - Prob. 6.21PCh. 6 - Prob. 6.22PCh. 6 - Prob. 6.23PCh. 6 - Prob. 6.24PCh. 6 - Prob. 6.25PCh. 6 - Prob. 6.26APCh. 6 - Prob. 6.27APCh. 6 - Prob. 6.28APCh. 6 - Prob. 6.29APCh. 6 - Prob. 6.30APCh. 6 - Prob. 6.31APCh. 6 - Prob. 6.32APCh. 6 - Prob. 6.33APCh. 6 - Prob. 6.34APCh. 6 - Prob. 6.35APCh. 6 - Prob. 6.36APCh. 6 - Prob. 6.37APCh. 6 - Prob. 6.38APCh. 6 - Prob. 6.39APCh. 6 - Prob. 6.40APCh. 6 - Prob. 6.41APCh. 6 - Prob. 6.42APCh. 6 - Prob. 6.43APCh. 6 - Prob. 6.44APCh. 6 - Prob. 6.45APCh. 6 - Prob. 6.46APCh. 6 - Prob. 6.47APCh. 6 - Prob. 6.48APCh. 6 - Prob. 6.49APCh. 6 - Prob. 6.50APCh. 6 - Prob. 6.51APCh. 6 - Prob. 6.52APCh. 6 - Prob. 6.53APCh. 6 - Prob. 6.54AP
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Similar questions
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- How do you account for the difference in energies between the two staggered conformations of 1,2-dichloroethane? How about for the two eclipsed conformations? Draw all four conformations and, on your drawing, indicate sources of strain – torsional, steric (gauche), steric eclipsed.arrow_forward(b) Classify the following two pairs of structures as conformational or configurational isomers. Explain your answer. and HO, OH il. and ноarrow_forward2. Draw and name the cis and trans (or Z and E) isomers of those that do.(a) hex-3-enearrow_forward
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