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

Pushing Electrons
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ISBN:9781133951889
Author:Weeks, Daniel P.
Publisher:Weeks, Daniel P.
Chapter3: Mechanisms
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**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.
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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