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Predict the product(s) and show the complete electron-pushing mecha- nism for each of the following dissolving metal reductions. (a) H3CC=CCH₂CH3 (b) (c) CECH Li NH3 ND3 -C=C-CH3 Li NH3

Predict the product(s) and show the complete electron-pushing mecha- nism for each of the following dissolving metal reductions. (a) H3CC=CCH₂CH3 (b) (c) CECH Li NH3 ND3 -C=C-CH3 Li NH3

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ISBN:9781305957404
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Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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In depth explanation of each, please. 

**Title: Understanding Dissolving Metal Reductions in Organic Chemistry** **Objective:** Predict the product(s) and illustrate the complete electron-pushing mechanism for each of the following dissolving metal reductions. **Reactions:** 1. **Reaction (a):** - Starting Material: H₃CC≡CCH₂CH₃ - Reagents: - Lithium (Li) - Ammonia (NH₃) - Description: This reaction involves the reduction of an alkyne to a trans-alkene using lithium in liquid ammonia. The electron-pushing involves the transfer of electrons from lithium to the alkyne, leading to the formation of a radical anion intermediate which then abstracts a proton from ammonia. 2. **Reaction (b):** - Starting Material: ![Image: Isopropylacetylene](Isopropylacetylene-structure) - Reagents: - Lithium (Li) - Deuterated ammonia (ND₃) - Description: Similar to (a), this reaction reduces an alkyne to a trans-alkene, but deuterated ammonia is used, incorporating deuterium into the final product. The mechanism involves a single-electron transfer and subsequent deuteration steps. 3. **Reaction (c):** - Starting Material: ![Image: Phenylpropyne](Phenylpropyne-structure) - Reagents: - Lithium (Li) - Ammonia (NH₃) - Description: This reaction reduces a phenyl-substituted alkyne. The electron-pushing mechanism includes the formation of a radical anion, followed by protonation, leading to the trans-alkene. **Mechanism Overview:** For each reaction, the lithium provides electrons that lead to the formation of a radical intermediate. Ammonia acts as a proton source, stabilizing the intermediate and facilitating the formation of the alkene. This method is particularly effective for selectively synthesizing trans-alkenes from alkynes.
Transcribed Image Text:**Title: Understanding Dissolving Metal Reductions in Organic Chemistry** **Objective:** Predict the product(s) and illustrate the complete electron-pushing mechanism for each of the following dissolving metal reductions. **Reactions:** 1. **Reaction (a):** - Starting Material: H₃CC≡CCH₂CH₃ - Reagents: - Lithium (Li) - Ammonia (NH₃) - Description: This reaction involves the reduction of an alkyne to a trans-alkene using lithium in liquid ammonia. The electron-pushing involves the transfer of electrons from lithium to the alkyne, leading to the formation of a radical anion intermediate which then abstracts a proton from ammonia. 2. **Reaction (b):** - Starting Material: ![Image: Isopropylacetylene](Isopropylacetylene-structure) - Reagents: - Lithium (Li) - Deuterated ammonia (ND₃) - Description: Similar to (a), this reaction reduces an alkyne to a trans-alkene, but deuterated ammonia is used, incorporating deuterium into the final product. The mechanism involves a single-electron transfer and subsequent deuteration steps. 3. **Reaction (c):** - Starting Material: ![Image: Phenylpropyne](Phenylpropyne-structure) - Reagents: - Lithium (Li) - Ammonia (NH₃) - Description: This reaction reduces a phenyl-substituted alkyne. The electron-pushing mechanism includes the formation of a radical anion, followed by protonation, leading to the trans-alkene. **Mechanism Overview:** For each reaction, the lithium provides electrons that lead to the formation of a radical intermediate. Ammonia acts as a proton source, stabilizing the intermediate and facilitating the formation of the alkene. This method is particularly effective for selectively synthesizing trans-alkenes from alkynes.
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Step 1: Introduction tothe reagent Li in liquid NH3

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