Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 4, Problem 36P
Interpretation Introduction
Interpretation:
The absolute configuration of
Concept introduction:
The absolute configuration (R/S) at a chiral carbon is determined on the basis of Cahn-Ingold-Prelog (CIP) rules.
If atom/group priorities excluding the lowest priority group follow a clockwise path, the absolute configuration is R. If the path followed is counterclockwise, the absolute configuration is S.
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Consider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide.
(a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds.
(b) Then analyze the stereochemistry of the product.
racemic
chiral
achiral
(1R, 3S)
(1R, 3R)
(1S, 3S)
The NMR spectrum of bromocyclohexane indicates a low field signal (1H) at δ 4.16. To room temperature, this signal is a singlet, but at -75 ° C it separates into two peaks of unequal area (but totaling one proton): δ 3.97 and δ 4.64, in ratio 4.6: 1.0. How do you explain the doubling in two peaks? According to the generalization of the previous problem, what conformation of the molecule predominates (at -75 ° C)? What percentage of the molecules does it correspond to?
Solve all parts otherwise down vote and hand written solution
1, part A) We observe 6 carbon stereocenters in the molecule below. Indicate each stereocenter, and give the absolute S or R configuration.
1, part B) Indicate each stereoisomer in this molecule, and give the absolute S or R configuration. Then, indicate E or Z configuration of all alkenes in it (*ignoring aromatic ring*).
Chapter 4 Solutions
Organic Chemistry - Standalone book
Ch. 4.2 - Examine the following for chirality centers:Ch. 4.2 - Prob. 2PCh. 4.3 - Prob. 3PCh. 4.3 - Prob. 4PCh. 4.4 - Prob. 5PCh. 4.4 - Prob. 6PCh. 4.5 - Does the molecular model shown represent...Ch. 4.6 - Assign absolute configurations as R or S to each...Ch. 4.6 - Draw three-dimensional representations ofCh. 4.7 - Prob. 10P
Ch. 4.7 - Using the Fischer projection of (R)-2-butanol...Ch. 4.8 - Prob. 12PCh. 4.9 - Prob. 13PCh. 4.9 - Prob. 14PCh. 4.10 - Prob. 15PCh. 4.10 - Draw Fischer projections of the four...Ch. 4.10 - Prob. 17PCh. 4.11 - A meso stereoisomer is possible for one of the...Ch. 4.11 - One of the stereoisomers of...Ch. 4.12 - Prob. 20PCh. 4.12 - Prob. 21PCh. 4.13 - Prob. 22PCh. 4.13 - Prob. 23PCh. 4.13 - Prob. 24PCh. 4.14 - Prob. 25PCh. 4 - Prob. 26PCh. 4 - Including stereoisomers, write structural formulas...Ch. 4 - Prob. 28PCh. 4 - Prob. 29PCh. 4 - Prob. 30PCh. 4 - Prob. 31PCh. 4 - Prob. 32PCh. 4 - Prob. 33PCh. 4 - Prob. 34PCh. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - Prob. 37PCh. 4 - Prob. 38PCh. 4 - Prob. 39PCh. 4 - (-)-Menthol is the most stable stereoisomer of...Ch. 4 - Prob. 41PCh. 4 - Prob. 42PCh. 4 - (a) An aqueous solution containing 10 g of...Ch. 4 - Prob. 44DSPCh. 4 - Prob. 45DSPCh. 4 - Consider two chemical changes: one occurring at a...Ch. 4 - Consider two chemical changes: one occurring at a...Ch. 4 - Prob. 48DSPCh. 4 - Consider two chemical changes: one occurring at a...Ch. 4 - Consider two chemical changes: one occurring at a...
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