In the elimination of a vicinal dihalide to yield an internal alkyne, two equivalents of NANH2 are required-one for each equivalent of HX that is eliminated. When the product is a terminal alkyne, however, three equivalents of NaNH2 are required. Explain why. Br 2 equiv NaNH, Br Br Br 1.3 equiv NaNH, 2. H,0
In the elimination of a vicinal dihalide to yield an internal alkyne, two equivalents of NANH2 are required-one for each equivalent of HX that is eliminated. When the product is a terminal alkyne, however, three equivalents of NaNH2 are required. Explain why. Br 2 equiv NaNH, Br Br Br 1.3 equiv NaNH, 2. H,0
Chapter3: Mechanisms
Section: Chapter Questions
Problem 29EQ
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Transcribed Image Text:**10.59** In the elimination of a vicinal dihalide to yield an internal alkyne, two equivalents of NaNH₂ are required—one for each equivalent of HX that is eliminated. When the product is a terminal alkyne, however, three equivalents of NaNH₂ are required. Explain why.
**Diagrams Explanation:**
1. **First Reaction:**
- The starting material is a brominated alkane with vicinal bromine atoms.
- Two equivalents of sodium amide (NaNH₂) are used.
- The resulting product is an internal alkyne, showing that two HX molecules have been eliminated.
2. **Second Reaction:**
- The starting material is another vicinal dihalide similar to the first.
- Here, three equivalents of NaNH₂ are used, followed by the addition of water (H₂O).
- The resulting product is a terminal alkyne, indicating that an additional step involving the removal of a proton from the terminal alkyne is required, thus explaining the need for the third equivalent of NaNH₂.
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