1. For the following compounds, find and mark the chirality centers and state whether the molecule as a whole is chiral or achiral. Be sure to consider resonance structures when determining your answers.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
Question
1. For the following compounds, find and mark the chirality centers and state whether the molecule as a whole is chiral or achiral. Be sure to consider resonance structures when determining your answers.

(a) A two-carbon molecule with one fluorine (F) and one chlorine (Cl) attached.

(b) A three-carbon molecule with two chlorine (Cl) atoms attached to the second carbon.

(c) A three-carbon chain with a ketone group (O) attached to the second carbon and a hydroxyl group (OH) attached to the third carbon.

(d) A benzene ring with a chlorine (Cl) and a methyl group (CH3) on adjacent carbon atoms.

(e) A benzene ring with two chlorine (Cl) atoms and a methyl (CH3) group attached.

(f) A bicyclic compound with an oxygen (O) atom, a nitrogen (N) atom with a positive charge, and a lone pair shown on a nitrogen adjacent to another nitrogen atom.

When analyzing these compounds for chirality, it's important to identify any carbon atoms that have four different groups attached, as these are potential chirality centers. Additionally, the overall symmetry and potential for resonance should be considered when determining if the molecule is chiral or achiral as a whole.
Transcribed Image Text:1. For the following compounds, find and mark the chirality centers and state whether the molecule as a whole is chiral or achiral. Be sure to consider resonance structures when determining your answers. (a) A two-carbon molecule with one fluorine (F) and one chlorine (Cl) attached. (b) A three-carbon molecule with two chlorine (Cl) atoms attached to the second carbon. (c) A three-carbon chain with a ketone group (O) attached to the second carbon and a hydroxyl group (OH) attached to the third carbon. (d) A benzene ring with a chlorine (Cl) and a methyl group (CH3) on adjacent carbon atoms. (e) A benzene ring with two chlorine (Cl) atoms and a methyl (CH3) group attached. (f) A bicyclic compound with an oxygen (O) atom, a nitrogen (N) atom with a positive charge, and a lone pair shown on a nitrogen adjacent to another nitrogen atom. When analyzing these compounds for chirality, it's important to identify any carbon atoms that have four different groups attached, as these are potential chirality centers. Additionally, the overall symmetry and potential for resonance should be considered when determining if the molecule is chiral or achiral as a whole.
Expert Solution
Step 1: Write down the conditions for molecule to be chiral

For a molecule to be chiral, elements of symmetry like the plane of symmetry and the inversion centre must be absent.

A plane of symmetry is a plane passing through the molecule such that one half of the molecule is exactly the mirror image of the other half. An inversion center is a point at the center of the molecule such that the same groups or atoms are present on either side of the point.

steps

Step by step

Solved in 3 steps with 1 images

Blurred answer
Knowledge Booster
Stereochemistry in Organic Reactions
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
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY