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

1. A Review of General Chemistry

Hybridization

Organic Chemistry

1. A Review of General Chemistry

Hybridization

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6:26 minutes

Problem 69

Textbook Question

In which orbitals are the lone pairs in nicotine?

Verified step by step guidance

Step 1: Analyze the structure of nicotine. Nicotine contains two nitrogen atoms, each with lone pairs of electrons. One nitrogen is part of a pyridine ring, and the other is part of a pyrrolidine ring.

Step 2: Determine the hybridization of the nitrogen atoms. The nitrogen in the pyridine ring is sp2 hybridized because it is part of an aromatic system, while the nitrogen in the pyrrolidine ring is sp3 hybridized because it is part of a saturated ring system.

Step 3: Consider the orbital location of the lone pairs. For the sp2 hybridized nitrogen in the pyridine ring, the lone pair resides in an sp2 orbital, which is oriented in the plane of the ring. For the sp3 hybridized nitrogen in the pyrrolidine ring, the lone pair resides in an sp3 orbital, which is tetrahedrally oriented.

Step 4: Note the implications of aromaticity. The lone pair on the sp2 hybridized nitrogen does not participate in the aromatic π-system of the pyridine ring because it is localized in the sp2 orbital.

Step 5: Summarize the orbital locations. The lone pair on the pyridine nitrogen is in an sp2 orbital, and the lone pair on the pyrrolidine nitrogen is in an sp3 orbital.

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Key Concepts

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

Molecular Orbitals

Molecular orbitals are formed by the combination of atomic orbitals when atoms bond together. In nicotine, the arrangement of these orbitals determines the distribution of electrons, including lone pairs. Understanding how these orbitals overlap helps in visualizing the electron density and the geometry of the molecule.

Lone Pairs

Lone pairs are pairs of valence electrons that are not involved in bonding and are localized on a single atom. In nicotine, the presence of lone pairs affects the molecule's shape and reactivity. Identifying the location of these lone pairs is crucial for predicting the molecule's behavior in chemical reactions.

Hybridization

Hybridization is the concept of mixing atomic orbitals to form new hybrid orbitals that can accommodate bonding and lone pairs. In nicotine, understanding the hybridization of the nitrogen atom helps determine the geometry and orientation of the lone pairs. This concept is essential for predicting molecular shape and reactivity.