Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

5. Chirality

Non-Carbon Chiral Centers

Organic Chemistry

5. Chirality

Non-Carbon Chiral Centers

Previous problemNext problem

3:57 minutes

Problem 85

Textbook Question

Butaclamol is a potent antipsychotic that has been used clinically in the treatment of schizophrenia. How many asymmetric centers does it have?

Verified step by step guidance

Step 1: Identify the definition of an asymmetric center. An asymmetric center (or chiral center) is a carbon atom that is bonded to four different groups or atoms.

Step 2: Examine the structure of Butaclamol provided in the image. Look for carbon atoms that are bonded to four distinct groups. Pay attention to stereochemical indicators such as wedges and dashed bonds, which denote 3D orientation.

Step 3: Locate the carbon atom attached to the hydroxyl group (OH), the tert-butyl group (C(CH3)3), a hydrogen atom, and the rest of the ring structure. This carbon is an asymmetric center because it is bonded to four different groups.

Step 4: Identify the second asymmetric center in the structure. Look for another carbon atom with stereochemical indicators (wedge and dashed bonds) that is bonded to four distinct groups. In this case, the carbon bonded to the nitrogen atom, a hydrogen atom, and two different ring systems qualifies as an asymmetric center.

Step 5: Count the total number of asymmetric centers in the molecule. Based on the analysis, there are two asymmetric centers in Butaclamol.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Asymmetric Centers

Asymmetric centers, or chiral centers, are carbon atoms that are bonded to four different substituents, leading to non-superimposable mirror images known as enantiomers. The presence of asymmetric centers in a molecule is crucial for determining its stereochemistry, which can significantly influence its biological activity and interactions.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this arrangement affects their chemical properties and reactions. Understanding stereochemistry is essential in organic chemistry, especially for compounds like Butaclamol, as different stereoisomers can exhibit different pharmacological effects.

Molecular Structure Analysis

Molecular structure analysis involves examining the arrangement of atoms within a molecule, often using techniques like spectroscopy or X-ray crystallography. This analysis helps identify features such as asymmetric centers, which are critical for understanding the compound's reactivity and interactions in biological systems.

Watch next

Master Understanding Other Chiral Atoms with a bite sized video explanation from Johnny

Start learning