Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 5.7, Problem 18P
Does the following structure represent a meso compound? If so, indicate the symmetry plane.
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For each compound, determine whether the molecule has an internal mirror plane of symmetry. If it does, draw the mirror plane on a three-dimensional drawing of the molecule. If the molecule does not have an internal mirror plane, determine whether the structure is chiral. trans-1,2dibromocyclobutane
Compounds with several chiral centres may have configurations referred to as meso. Meso configurations arise when the molecule can adopt a configuration with an internal mirror plane. When this occurs, the mirror image of a molecule with an internal mirror plane is an identical configuration. Thus, even though the molecule may possess several chiral centres, they are reflection of each other (within the molecule) thus resulting in an achiral meso form.
This occurs for example for tartaric acid (Figure 3.1). Because of this, tartaric acid only has three stereoisomers instead of four. It has the two chiral (R,R) and (S,S) enantiomers, and the meso form.
Figure 3.1. Stereoisomers of tartaric acid.
Given the information above on meso forms, how many different stereoisomers do compounds A to D (Figure 3.2) have?
Figure 3.2. Structure of compounds A, B, C and D.
To the following statement, answer true or false and explain your answer.
Q)To be meso, a molecule must have at least two chiral centers
Chapter 5 Solutions
Organic Chemistry
Ch. 5.2 - Prob. 1PCh. 5.2 - Prob. 2PCh. 5.2 - Prob. 3PCh. 5.2 - Prob. 4PCh. 5.3 - Is cocaine (Worked Example 5-2) dextrorotatory or...Ch. 5.3 - Prob. 6PCh. 5.5 - Prob. 7PCh. 5.5 - Prob. 8PCh. 5.5 - Prob. 9PCh. 5.5 - Assign R or S configuration to the chirality...
Ch. 5.5 - Draw a tetrahedral representation of...Ch. 5.5 - Prob. 12PCh. 5.6 - One of the following molecules (a)–(d) is...Ch. 5.6 - Prob. 14PCh. 5.6 - Assign R or S configuration to each chirality...Ch. 5.7 - Prob. 16PCh. 5.7 - Which of the following have a meso form? (Recall...Ch. 5.7 - Does the following structure represent a meso...Ch. 5.8 - Prob. 19PCh. 5.8 - Prob. 20PCh. 5.9 - Prob. 21PCh. 5.11 - Prob. 22PCh. 5.11 - Prob. 23PCh. 5.11 - The lactic acid that builds up in tired muscles is...Ch. 5.11 - The aconitase-catalyzed addition of water to...Ch. 5.SE - Which of the following structures are identical?...Ch. 5.SE - Prob. 27VCCh. 5.SE - Prob. 28VCCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Prob. 30VCCh. 5.SE - Prob. 31APCh. 5.SE - Which of the following compounds are chiral? Draw...Ch. 5.SE - Prob. 33APCh. 5.SE - Eight alcohols have the formula C5H12O. Draw them....Ch. 5.SE - Draw compounds that fit the following...Ch. 5.SE - Prob. 36APCh. 5.SE - Prob. 37APCh. 5.SE - Prob. 38APCh. 5.SE - What is the stereochemical configuration of the...Ch. 5.SE - Prob. 40APCh. 5.SE - Prob. 41APCh. 5.SE - Prob. 42APCh. 5.SE - Prob. 43APCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Prob. 46APCh. 5.SE - Assign R or S configuration to each chirality...Ch. 5.SE - Assign R or S configurations to the chirality...Ch. 5.SE - Assign R or S stereochemistry to the chirality...Ch. 5.SE - Prob. 50APCh. 5.SE - Draw examples of the following: (a) A meso...Ch. 5.SE - Prob. 52APCh. 5.SE - Prob. 53APCh. 5.SE - Prob. 54APCh. 5.SE - On reaction with hydrogen gas by a platinum...Ch. 5.SE - Prob. 56APCh. 5.SE - Prob. 57APCh. 5.SE - One of the steps in fat metabolism is the...Ch. 5.SE - The dehydration of citrate to yield cis-aconitate,...Ch. 5.SE - The first step in the metabolism of glycerol,...Ch. 5.SE - One of the steps in fatty-acid biosynthesis is the...Ch. 5.SE - Prob. 62APCh. 5.SE - Draw tetrahedral representations of the two...Ch. 5.SE - The naturally occurring form of the amino acid...Ch. 5.SE - Prob. 65APCh. 5.SE - Prob. 66APCh. 5.SE - Prob. 67APCh. 5.SE - Allenes are compounds with adjacent carbon-carbon...Ch. 5.SE - Prob. 69APCh. 5.SE - Prob. 70APCh. 5.SE - How many stereoisomers of...Ch. 5.SE - Draw both cis- and trans-1,4-dimethylcyclohexane...Ch. 5.SE - Draw both cis- and trans-1,3-dimethylcyclohexane...Ch. 5.SE - cis-1,2-Dimethylcyclohexane is optically inactive...Ch. 5.SE - Prob. 75APCh. 5.SE - Prob. 76APCh. 5.SE - Prob. 77AP
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- For each compound, determine whether the molecule has an internal mirror plane of symmetry. If it does, draw the mirror plane on a three-dimensional drawing of the molecule. If the molecule does not have an internal mirror plane, determine whether the structure is chiral.1,2-dichloropropanearrow_forwardThe MOE results and a discussion pertaining to the conformation of Thioflavin T at low potential energies. At low energies, the conformation of ThT cannot be coplanar, that is, the dihedral angle cannot be 0. Why not?arrow_forwardSN? displacement of a chiral molecule occurs with inversion of configuration. A True B) Falsearrow_forward
- Molecules with a plane of symmetry between the chiral centers are achiral and meso. Determine if this molecule has a plane of symmetry and if it is meso. *****||||| A) There is a plane of symmetry in this molecule and it is achiral, but it is not meso. B) There is a plane of symmetry in this molecule and it is achiral. This molecule is meso. C) There is no plane of symmetry in this molecule and it is achiral. This molecule is not meso. D) There is no plane of symmetry in this molecule and it is chiral. It is not meso. E) There is no plane of symmetry in this molecule and it is chiral. It is meso. +arrow_forwardIs there a chiral molecule without chiral center. If yes, are these compounds chiral or achiral.arrow_forwardN2O4 is planar. Show that it possesses three planes of symmetry.arrow_forward
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