Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Question
Chapter 5, Problem 5.11YT
Interpretation Introduction
(a)
Interpretation:
Whether the compound
Concept introduction:
Chiral molecules are molecules in which carbon atom contain four different groups on it. The carbon atom which contains four different groups is known as the chiral center of the molecule.
Interpretation Introduction
(b)
Interpretation:
The compound
Concept introduction:
When two compounds are superimposable mirror images, then the compound is same but if they are not superimposable and mirror images of each other, then they are diastereomers of each other. These diastereomers are stereoisomers which are not mirror images of each other. To be stereoisomers, they must contain the same molecular formula, be different molecules, and have same connectivity.
Interpretation Introduction
(c)
Interpretation:
Chair flipping of
Concept introduction:
When two compounds are superimposable mirror images, then the compound is same but if they are not superimposable mirror images of each other, then they are diastereomers of each other. These diastereomers are stereoisomers which are not mirror images of each other. To be stereoisomers, they must contain same molecular formula, be different molecules, and have same connectivity.
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3) Draw Fischer projections for all stereoisomers of the following compound:
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You should find two meso structures and one pair of enantiomers. Please clearly indicate these designations on each of your structures. For each
stereoisomer, star all chirality centers, and indicate any mirror planes in (or between) your diagrams as dashed lines. For ONE stereoisomer of your
choosing, assign R/S notation, being sure to show your priorities 1-4.
F) Circle the letter corresponding to the relationship of each pair of structures:
Identical (I), Conformers (C), Enantiomers (E) (enantiomers can have different
conformations). FIRST... determine the absolute configuration of chiral centers.
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Problem: Use the molecules below to answer the questions. (a) List one pair of enantiomers, if
any. (b) List one pair of diastereomers, if any. (c) List one meso compound, if any. (d) How many
total configurational isomers are possible for compound 2?
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Chapter 5 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
Ch. 5 - Prob. 5.1PCh. 5 - Prob. 5.2PCh. 5 - Prob. 5.3PCh. 5 - Prob. 5.4PCh. 5 - Prob. 5.5PCh. 5 - Prob. 5.6PCh. 5 - Prob. 5.7PCh. 5 - Prob. 5.8PCh. 5 - Prob. 5.9PCh. 5 - Prob. 5.10P
Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Prob. 5.13PCh. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Prob. 5.18PCh. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Prob. 5.25PCh. 5 - Prob. 5.26PCh. 5 - Prob. 5.27PCh. 5 - Prob. 5.28PCh. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Prob. 5.34PCh. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Prob. 5.37PCh. 5 - Prob. 5.38PCh. 5 - Prob. 5.39PCh. 5 - Prob. 5.40PCh. 5 - Prob. 5.41PCh. 5 - Prob. 5.42PCh. 5 - Prob. 5.43PCh. 5 - Prob. 5.44PCh. 5 - Prob. 5.45PCh. 5 - Prob. 5.46PCh. 5 - Prob. 5.47PCh. 5 - Prob. 5.48PCh. 5 - Prob. 5.49PCh. 5 - Prob. 5.50PCh. 5 - Prob. 5.51PCh. 5 - Prob. 5.52PCh. 5 - Prob. 5.53PCh. 5 - Prob. 5.54PCh. 5 - Prob. 5.55PCh. 5 - Prob. 5.56PCh. 5 - Prob. 5.57PCh. 5 - Prob. 5.58PCh. 5 - Prob. 5.59PCh. 5 - Prob. 5.60PCh. 5 - Prob. 5.61PCh. 5 - Prob. 5.62PCh. 5 - Prob. 5.63PCh. 5 - Prob. 5.64PCh. 5 - Prob. 5.65PCh. 5 - Prob. 5.66PCh. 5 - Prob. 5.67PCh. 5 - Prob. 5.68PCh. 5 - Prob. 5.69PCh. 5 - Prob. 5.70PCh. 5 - Prob. 5.71PCh. 5 - Prob. 5.72PCh. 5 - Prob. 5.73PCh. 5 - Prob. 5.74PCh. 5 - Prob. 5.75PCh. 5 - Prob. 5.76PCh. 5 - Prob. 5.77PCh. 5 - Prob. 5.78PCh. 5 - Prob. 5.79PCh. 5 - Prob. 5.1YTCh. 5 - Prob. 5.2YTCh. 5 - Prob. 5.3YTCh. 5 - Prob. 5.4YTCh. 5 - Prob. 5.5YTCh. 5 - Prob. 5.6YTCh. 5 - Prob. 5.7YTCh. 5 - Prob. 5.8YTCh. 5 - Prob. 5.9YTCh. 5 - Prob. 5.10YTCh. 5 - Prob. 5.11YTCh. 5 - Prob. 5.12YTCh. 5 - Prob. 5.13YTCh. 5 - Prob. 5.14YTCh. 5 - Prob. 5.15YTCh. 5 - Prob. 5.16YTCh. 5 - Prob. 5.17YT
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- chiral. If you were able to make another molecule that is a mirror image of the chiral molecule, the mirror image and the original molecule will be non-superimposable. i.e. the atoms surrounding carbon won't completely align. The lack of alignment of the suround atom makes the two molecules different from each other. The central carbon must be surrounded by 4 different groups. The chiral carbon is highlighted. CH;CH) CHICH2 CH3-C-CH2-CHy OH CH) miror The 3D structure of the above molecule focuses on the chiral carbon and the bond surrounding the chiral carbon. The molecule on the left is different from the molecule on the right (mirror image) because they are non-superimposable. H. CH3-C-COOH HOOC COOH CH NH2 NH2 mimor Answer the following questions: 1. Draw five structural isomers for hexane, CHe. Isomer 3 Isomer 2 Isomer 1 Isomer 5 Isomer 4 2. Draw three structural isomers as possible for CHO.arrow_forwardFor the compounds provided below. Identify the three stereogenic centers in the molecule and indicate R or S configuration designations. (HINT: Add your hydrogens and check for 3D positioning using wedge and dash when applies). H₂CO Dextromethorphan (cough suppressant)arrow_forwardMay I have an explanation for how you know which atom at the chiral center is wedged or dashed for both before and after rotating? Unless the problem specifically shows which is wedged or dashed from the get-go, I'm pretty much guessing which atom is sticking out or away after determining the CIP 1-4 step.arrow_forward
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