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Draw the neutral organic product for the following reaction. Show stereochemistry clearly. Draw the neutral organic...

Draw the neutral organic product for the following reaction. Show stereochemistry clearly.

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Draw the neutral organic product for the following reaction. Show stereochemistry clearly.
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Answer #1
Concepts and reason

Reduction of Alkynes to trans-Alkenes:

An alkyne is an unsaturated hydrocarbon which has a carbon-carbon () triple bond. The carbon-carbon triple bond can react with sodium or lithium in the presence of liquid ammonia or amine solvent to give a trans-alkene containing a carbon-carbon (C=C
) double bond.

Anti-addition:

Anti-addition is defined as the addition of two substituents to opposite sides of a triple bond to form the anti-addition product.

Fundamentals

Reaction of alkyne with Li metal:

An alkyne is reduced to a trans-alkene with lithium metal in an ethyl amine solvent which can act as a reducing agent, followed by the addition of ammonium chloride salt. For example,

R-C5
-R
1. Li, CH3CH2NH2
–
2. NH4Cl
Alkyne
R
Trans Alkene

Mechanism:

nm
-
Ice
cream
R
-c
ác-R
Li
–
c=ce L:
CH3NH
Alkyne
Ć
+ CH3NH® Li®
=
+ CH3NH® Li®
H
R.
trans-alkene
C2H5NH

Formation of the radical anion intermediate:

C=
C-
c=ce L®
Alkyne

Formation of the vinyl radical:

c=ce L®
CHÚNH
+ C2H5NHPL:

Formation of the vinylic anion:

Formation for the trans-alkene:

- Bing
+ C2H3NH® Li®
C2H5NH
trans-alkene
anti addition product

Ans:

| 1. 2 Li, C,H,NH, -78 °C
-
2. NHCl
0-
Trans product

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