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Question

Provide reagents for the following transformation.
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Solution

The reagents are as given below.
A: Lindlar's catalyst orNa/NH3(l) selectively reduces carbon carbon triple bond to carbon carbon double bond.
B: HBr(excess) adds two molecules to the carbon carbon triple bond. Bromine is added to carbon atom carrying maximum
substituents.
C:HBr (peroxide) adds a molecule of HBr to carbon carbon triple bond according to Anti Markovnikov's Rule.Bromine is
added to the carbon atom having least substituents.
D: Lindlar's catalyst then HBr(ROOR). Lindlars catalyst selectively reduces triple bond to double bond. Then a molecule
of HBr is added according to Anti Markovnikov's Rule as peroxide is present..
E: B2H6H2O2/NaOH adds a molecule of water followed by keto enol tautomerism. This is hydroboration
oxidation reaction.
F: H2SO4(aq)/HgSO4 adds a molecule of water followed by keto enol tautomerism. This is hydration
reaction.
G: Lindlar's catalyst then HBr. Lindlars catalyst selectively reduces triple bond to double bond. Then a molecule of HBr is
added according to Markovnikov's Rule.

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