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Predict the product(s) and show the complete electron-pushing mechanism for each of the following dissolving metal reductions.

Short Answer

Expert verified

a).

b).

c).

Step by step solution

01

General mechanism for Li, NH3 with alkyne

The Lithium atom acts as an electron donor. acts as a proton donor in the reaction. The general mechanism for the reduction of alkynes is given below. Reduction with gives products with trans stereochemistry.

02

Reaction of given alkyne with lithium metal and ammonia

In the first step of the reaction, the Li atom donates an electron to form Li+ion and one pi bond breaks. This results in the generation of a radical on one carbon atom along with the formation of carbanion on the adjacent carbon. The carbanion formed extracts a proton from NH3. In the following steps the Lithium atom donates one electron. Therefore the carbon radical forms a carboanion. The carboanion form abstracts a proton from NH3 to give the required alkene.

03

Reaction of given alkyne with lithium metal and ammonia

In the first step of the reaction, the Li atom donates an electron to form Li3+ion and one pi bond breaks. This results in the generation of a radical on one carbon atom along with the formation of carbanion on the adjacent carbon. The carbanion formed extracts a proton from ND3. In the following steps the Lithium atom donates one electron. Therefore the carbon radical forms a carbanion. The carbonaton form abstracts a proton from NiD3to give the required alkene.

04

Reaction of given alkyne with lithium metal and ammonia

In the first step of the reaction, the Li atom donates an electron to form Li+ion and one pi bond breaks. This results in the generation of a radical on one carbon atom along with the formation of carbanion on the adjacent carbon. The carbanion formed extracts a proton from NH3. In the following steps the Lithium atom donates one electron. Therefore the carbon radical forms a carbanion. The carboanion form abstracts a proton from NH3to give the required alkene.

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Show the structures of the fragments you would expect in the mass

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