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

Sigma and Pi Bonds

Organic Chemistry

1. A Review of General Chemistry

Sigma and Pi Bonds

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2:24 minutes

Problem 3a

Textbook Question

How many s bond orbitals are available for overlap with the vacant p orbital in
1. the isobutyl cation?
2. the n-butyl cation?
3. the sec-butyl cation?

Verified step by step guidance

Step 1: Understand the concept of sigma (σ) bonds and vacant p orbitals. Sigma bonds are formed by the direct overlap of orbitals, and a vacant p orbital is an unoccupied orbital that can potentially overlap with adjacent orbitals. In carbocations, the positively charged carbon has a vacant p orbital.

Step 2: Analyze the structure of the isobutyl cation. The isobutyl cation has a branched structure with the positively charged carbon atom connected to three other carbons. Identify the number of σ bonds directly adjacent to the positively charged carbon that can overlap with the vacant p orbital.

Step 3: Examine the structure of the n-butyl cation. The n-butyl cation has a straight-chain structure with the positively charged carbon atom at the end of the chain. Determine the number of σ bonds adjacent to the positively charged carbon that can overlap with the vacant p orbital.

Step 4: Investigate the structure of the sec-butyl cation. The sec-butyl cation has a secondary carbon as the positively charged center, meaning it is connected to two other carbons and one hydrogen. Count the number of σ bonds adjacent to the positively charged carbon that can overlap with the vacant p orbital.

Step 5: Summarize the findings for each cation. For each structure, the number of σ bonds available for overlap with the vacant p orbital corresponds to the number of atoms directly bonded to the positively charged carbon. This includes both carbon and hydrogen atoms.

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Key Concepts

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

Hybridization

Hybridization is the process by which atomic orbitals mix to form new hybrid orbitals that can accommodate bonding. In organic chemistry, understanding the hybridization of carbon atoms is crucial, as it determines the geometry and types of bonds formed. For example, sp3 hybridization involves one s and three p orbitals, leading to tetrahedral geometry, while sp2 involves one s and two p orbitals, resulting in trigonal planar geometry.

Cation Stability

Cation stability refers to the relative stability of positively charged carbon species, which is influenced by factors such as hybridization and the surrounding substituents. Tertiary cations are generally more stable than secondary or primary cations due to hyperconjugation and inductive effects from alkyl groups. This stability affects the reactivity and formation of cations in organic reactions.

Orbital Overlap

Orbital overlap is the concept that describes how atomic orbitals combine to form bonds in molecules. In the context of cations, the overlap between s bond orbitals and vacant p orbitals is essential for understanding how these cations can stabilize or react. The extent of overlap influences bond strength and the overall stability of the resulting molecular structure.

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Related Practice

Textbook Question

Suppose a molecule is formed by the overlap of 16 atomic orbitals.

(a) How many molecular orbitals will be present?

(b) How many will be bonding?

Textbook Question

For the following partial structures, the σ bond is shown. Add the indicated number of π bonds, being sure to specify the orientation (that is, x, y, or z axis) of the p orbitals used.

(e)

Textbook Question

The molecular orbital picture of H₂ can be represented by the following diagram. Label σ and σ* on the diagram—that is, which is (a) and which is (b)? Which is lower in energy? Why?

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Textbook Question

Given the Lewis structures, indicate the direction of the dipole moment, if there is one.

(e)

Multiple Choice

In a double bond, which type of bond is formed by the overlap of p orbitals?

Multiple Choice

In the formation of sigma and pi bonds, which type of electrons are primarily involved?

Multiple Choice

What type of chemical bond is formed when two sulfur-containing chains are joined together?

Multiple Choice

In the context of molecular interactions, what type of bond is typically broken when mRNA separates from the DNA template during transcription?