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

3. Acids and Bases

Ranking Acidity

Organic Chemistry

3. Acids and Bases

Ranking Acidity

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3:22 minutes

Problem 66

Textbook Question

Tenormin, a member of the group of drugs known as beta-blockers, is used to treat high blood pressure and improve survival after a heart attack. It works by slowing down the heart to reduce its workload. Which atom in Tenormin is the most basic?

Verified step by step guidance

Step 1: Understand the concept of basicity in organic chemistry. Basicity refers to the ability of an atom to donate a pair of electrons, typically to a proton (H⁺). Atoms with lone pairs of electrons, such as nitrogen, oxygen, or sulfur, are often candidates for basicity.

Step 2: Analyze the structure of Tenormin (Atenolol). Tenormin contains functional groups such as amines, alcohols, and possibly ethers. Focus on identifying atoms with lone pairs of electrons that can act as bases.

Step 3: Evaluate the nitrogen atom in the amine group. Amines are typically more basic than oxygen-containing groups because nitrogen is less electronegative than oxygen, making its lone pair more available for protonation.

Step 4: Consider the environment around the nitrogen atom. If the nitrogen is part of a secondary or tertiary amine, its basicity may be influenced by steric hindrance or electronic effects from nearby groups.

Step 5: Compare the basicity of the nitrogen atom to other atoms in the molecule, such as oxygen in alcohol or ether groups. Oxygen atoms are generally less basic than nitrogen due to their higher electronegativity, which holds onto the lone pair more tightly.

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Key Concepts

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

Basicity in Organic Chemistry

Basicity refers to the ability of a compound to accept protons (H+) or donate electron pairs. In organic chemistry, basicity is influenced by the structure of the molecule, including the presence of electronegative atoms and the availability of lone pairs. A more basic atom typically has a higher electron density and is less hindered by steric factors.

Functional Groups in Beta-Blockers

Beta-blockers, like Tenormin, contain specific functional groups that influence their pharmacological properties. Common functional groups include amines, which can act as bases due to the presence of nitrogen atoms with lone pairs. Understanding the functional groups present in Tenormin is crucial for determining which atom may exhibit the highest basicity.

Structure-Activity Relationship (SAR)

The Structure-Activity Relationship (SAR) is a principle that explores how the chemical structure of a compound relates to its biological activity. In the case of Tenormin, analyzing its molecular structure helps identify which atoms contribute to its basicity and overall effectiveness as a beta-blocker. This relationship is essential for predicting how modifications to the structure can affect drug performance.

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