(a)
Interpretation:
The major product of the given reaction is to be predicted and a complete mechanism is to be provided.
Concept introduction:
Reactive metals like Na and Li dissolve in liquid ammonia. This is not a simple physical process. The atoms of the metal ionize and the electron lost is stabilized by extensive solvation by ammonia molecules. The solvated electron behaves like a radical even though it does not belong to a particular atom. It adds to one of the carbons of the triple bond of an
The carbanion is a strong nucleophile and a base. It extracts a proton from an ammonia molecule to form a neutral alkenyl radical and an amide (
Overall, the reaction is the addition of two hydrogen atoms to the triple bond to produce a trans alkene.
(b)
Interpretation:
The major product of the given reaction is to be predicted and a complete mechanism is to be provided.
Concept introduction:
Reactive metals like Na and Li dissolve in liquid ammonia. This is not a simple physical process. The atoms of the metal ionize and the electron lost is stabilized by extensive solvation by ammonia molecules. The solvated electron behaves like a radical even though it does not belong to a particular atom. It adds to one of the carbons of the triple bond of an alkyne. The bond order decreases to two, the carbon to which the electron adds becomes a highly reactive carbanion and the other carbon is converted to a radical. The configuration of the double bond is trans as a result of the steric repulsion between the two groups attached to the carbons of the initial triple bond.
The carbanion is a strong nucleophile and a base. It extracts a proton from an ammonia molecule to form a neutral alkenyl radical and an amide (
Overall, the reaction is the addition of two hydrogen atoms to the triple bond to produce a trans alkene.
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Chapter 25 Solutions
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
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