6) Which of the following compounds is meso? H₂C HC-C-H OH H₂C HO CH₂ H CH3 F HS SH Br & ||||| Br

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
icon
Concept explainers
Question
**6) Which of the following compounds is meso?**

The image presents four different chemical structures. 

1. The first structure is an open-chain molecule with the following groups arranged around the central carbon atoms:
   - One carbon atom is bonded to:
     - A hydroxyl group (OH) on the right.
     - A methyl group (CH3) above.
     - A hydrogen atom (H) below.
     - A hydroxyl group (HO) to the bottom left.
   - The second carbon atom is bonded to:
     - A methyl group (CH3) on the left.
     - A hydrogen atom (H) above.

2. The second structure is an open-chain molecule showing a central carbon atom with:
   - A chlorine atom (Cl) represented with dashed lines, indicating it is below the plane of the page.
   - A hydrogen atom (H) and a methyl group (CH3) bonded to the central carbon.
   - Another chlorine atom (Cl) represented with wedged lines, indicating it is above the plane of the page.
   - A second central carbon identical in structure with the first.

3. The third structure is an open-chain molecule with two central carbon atoms each bonded to:
   - A fluorine atom (F) with wedged lines, indicating they are above the plane of the page.
   - A fluorine atom (F) with dashed lines, indicating they are below the plane of the page.
   - A thiol group (SH) at one end and another thiol (HS) group on the other end.
   - A fluorine atom bonded in the middle.

4. The fourth structure is a cyclic compound (a ring) showing:
   - A pentagon shape, representing a five-membered ring.
   - Two hydrogen atoms (H) in the upward direction.
   - Two bromine atoms (Br) represented with wedge-and-dash bonds (one is wedged and the other is dashed), indicating different planes.

**Graph Analysis:**
- Each of the presented compounds needs to be evaluated using symmetry and plane of symmetry concepts to identify meso compounds.
- A meso compound is one which has multiple chiral centers but is superimposable on its mirror image and shows internal symmetry.

**Conclusion:**
Based on internal symmetry considerations, analyze each structure for meso characteristics by determining if it can be superimposed on its mirror image and possesses a plane of symmetry.
Transcribed Image Text:**6) Which of the following compounds is meso?** The image presents four different chemical structures. 1. The first structure is an open-chain molecule with the following groups arranged around the central carbon atoms: - One carbon atom is bonded to: - A hydroxyl group (OH) on the right. - A methyl group (CH3) above. - A hydrogen atom (H) below. - A hydroxyl group (HO) to the bottom left. - The second carbon atom is bonded to: - A methyl group (CH3) on the left. - A hydrogen atom (H) above. 2. The second structure is an open-chain molecule showing a central carbon atom with: - A chlorine atom (Cl) represented with dashed lines, indicating it is below the plane of the page. - A hydrogen atom (H) and a methyl group (CH3) bonded to the central carbon. - Another chlorine atom (Cl) represented with wedged lines, indicating it is above the plane of the page. - A second central carbon identical in structure with the first. 3. The third structure is an open-chain molecule with two central carbon atoms each bonded to: - A fluorine atom (F) with wedged lines, indicating they are above the plane of the page. - A fluorine atom (F) with dashed lines, indicating they are below the plane of the page. - A thiol group (SH) at one end and another thiol (HS) group on the other end. - A fluorine atom bonded in the middle. 4. The fourth structure is a cyclic compound (a ring) showing: - A pentagon shape, representing a five-membered ring. - Two hydrogen atoms (H) in the upward direction. - Two bromine atoms (Br) represented with wedge-and-dash bonds (one is wedged and the other is dashed), indicating different planes. **Graph Analysis:** - Each of the presented compounds needs to be evaluated using symmetry and plane of symmetry concepts to identify meso compounds. - A meso compound is one which has multiple chiral centers but is superimposable on its mirror image and shows internal symmetry. **Conclusion:** Based on internal symmetry considerations, analyze each structure for meso characteristics by determining if it can be superimposed on its mirror image and possesses a plane of symmetry.
Expert Solution
steps

Step by step

Solved in 3 steps with 1 images

Blurred answer
Knowledge Booster
Carbohydrates
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
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