Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
bartleby

Videos

Textbook Question
Book Icon
Chapter 5.7, Problem 18P

Does the following structure represent a meso compound? If so, indicate the symmetry plane.

Chapter 5.7, Problem 18P, Does the following structure represent a meso compound? If so, indicate the symmetry plane.

Blurred answer
Students have asked these similar questions
How many symmetry planes and symmetry axis in C3H8O. also is there a center of symmetry in C3H8O?
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.

Chapter 5 Solutions

Organic Chemistry

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
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole
Group Theory - Learn like Expert with 3D animation | Introduction for Beginners | ONE Chemistry; Author: One Chemistry;https://www.youtube.com/watch?v=Lz2ih8fkgDs;License: Standard YouTube License, CC-BY