Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 6, Problem 6.12P
Interpretation Introduction
Interpretation:
The observed optical rotation of the given solution of
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 as asymmetric or stereogenic centers. A chiral molecule is an optically active molecule. It rotates the plane of a plane polarized light. The observed optical rotation of a compound is given as,
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c) Label (if possible) the structure(s) in part (b) as either Z or E double bond isomers.
Recently, the Gademann research group from the University of Zurich,
completed the synthesis of (+)-Peyssonnosol, a complex natural product (shown below
on the left) which contains seven stereocenters. Briefly describe what the "(±)" symbol in
front of the synthesized natural product name means.
Me,
Ме
.Me Me
HO...
Me
...
Me
Synthesized
(±)-Peyssonnosol
Starting Materials Used
in Synthesis
In the acid-catalyzed dehydration of 2-methyl-1-propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon–oxygen bond in the alkyloxonium ion? What ion would be formed as a result of a methyl shift? Which pathway do you think will predominate, a hydride shift or a methyl shift?
The structure of A is shown below.
HO 3
-CH2CH=CH2
A
(i) Predict the possible number of stereoisomers A can have.
(ii) Draw the 3D structure of the (25, 3R, 5S) enantiomer showing its correct stereochemistry.
(iii) Calculate the specific rotation of each enantiomer in a mixture containing 10 mL (0.10 M) of (2S, 3R, 55) enantiomer and 30 mL (0.10 M) of (2R, 3S, 5R)
enantiomer. Given the specific rotation of the mixture = +4.8°.
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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