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...
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Transcribed Image Text:**Title: Understanding Organic Reactions: Formation of Alkyne**
**Introduction:**
In this exercise, we will explore the transformation of a vicinal dibromide into an alkyne using sodium amide (NaNH₂) as a base followed by treatment with an acid (H₃O⁺). This type of reaction is commonly encountered in organic synthesis to form carbon-carbon triple bonds.
**Reaction Details:**
1. **Starting Material:**
- The initial compound is a six-carbon chain with two bromine atoms attached to adjacent (vicinal) carbon atoms (vicinal dibromide).
2. **Reagents:**
- NaNH₂ (sodium amide), Δ (heat)
- H₃O⁺ (acidic workup)
3. **Mechanism:**
- The reaction proceeds through an elimination mechanism. Sodium amide (NaNH₂) acts as a strong base, abstracting hydrogen atoms and facilitating the removal of bromine atoms as bromide ions.
- The elimination of two equivalents of HBr leads to the formation of an alkyne.
4. **Product:**
- The final product is a linear alkyne, characterized by a carbon-carbon triple bond.
**Diagram Explanation:**
- **Reaction Scheme:**
- The starting dibromide on the left is transformed into an alkyne on the right.
- The arrow indicates the reaction progression, driven by the applied reagents.
**Conclusion:**
This transformation from a vicinal dibromide to an alkyne highlights the utility of strong bases in organic synthesis, allowing chemists to build complex molecular architectures with precise control over functional group placement.
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