Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 5, Problem 5.8YT
Interpretation Introduction
Interpretation:
It is to be proved that
Concept introduction:
An atom and its mirror image are directly opposite each other on opposite sides of the mirror. An atom and its mirror image are identical distances away from the mirror. When the mirror is perpendicular to the plane of the page, dash-wedge notation in the mirror image is identical to that in the original molecule. A molecule is chiral if the mirror image considering every orientation possible does not superimpose with the original molecule.
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Students have asked these similar questions
Consider the molecule shown here. (a) How many chiral
centers does it have? (b) How many total configurational
isomers are possible? Hint: Determine whether it is possible
for any of the configurational isomers to be meso.
OH
OH
OH
HO
TH.
OH
OH
OH
How many chiral centers are there in this molecule and identify them on the image? Is it delivered as one enantiomer or a mixture?
On b), I understand that we don't know which side of the molecule the Cl would attach on, but I was under the impression that we only show stereochemistry on a chiral center, and I do not see where the chiral center is on this molecule. Would you be able to explain this?
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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- Please also point out where the chiral centers are.arrow_forwardchiral. 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_forwardWhat is the lowest energy 3D conformation of the molecule in the image?arrow_forward
- Determine which of these are meso and non-meso.arrow_forwardAnalyze the structure of the two stereoisomers and then determine whether one or both of them is (are) chiral (s). Explain your reasoning.arrow_forwardIdentify any chiral centers within the 2 molecules and identify whether each molecule is chiral or archial. If it is chiral, explain whether you expect a single enantiomer or a mixture of enantiomers to be formed.arrow_forward
- 2. Is IR helpful to prove that limonene is optically active? Why or why not? Answer question here 3. If a sample is determined to be 75% of the (+) enantiomer, then what is the enantiomeric excess? Answer question here 4. An experiment is performed were the specific rotation was determined to be +52° for the resulting isolation (note this is not the observed rotation). If the enantiomerically pure compound has a literature rotation of +97°, then what is the percent of each enantiomer in the isolated mixture? Answer question here 5. Can you determine the percent R and S from the information given in questions 4? Explain. Answer question herearrow_forwardAssign R or S configuration around the two chiral carbons in the following molecule. - clearly show the priorities of the groups attached to each chiral carbon and how this resulted in your assigned configurationsarrow_forwardwhat is the absolute configuration on each of the chiral centers.arrow_forward
- 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? онно CH 3 он но H QH H CH3 CH 3 CH3 H OH но. „CH3 H он H H. "CH 3 H H "CH3 H H3C H3C 4 3 1arrow_forwardDraw the diastereomer of the molecule below.arrow_forwardDraw only the diastereomer(s) of the following moleculearrow_forward
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