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Question

Consider the following reactions-
The correct set of reagents for these reactions is :
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A
R1:H2/Lindlarcatalyst,R2:Na/liq.NH3,R3:(i)O3,(ii)H2O,R4:H2OH2SO4,HgSO4
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B
R1:H2/Lindlarcatalyst,R2:Na/liq.NH3,R3:H2O,H2SO4,HgSO4,R4:(i)O3,(ii)H2O
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C
R1:(i)O3,(ii)H2O,R2:H2OH2SO4,HgSO4,R3:Na/liq.NH3,R4:H2/Lindlarcatalyst
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D
R1:H2OH2SO4,HgSO4,R2:H2/Lindlarcatalyst,R3:(i)O3,(ii)H2O,R4:Na/liq.NH3
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Solution

The correct option is B R1:H2/Lindlarcatalyst,R2:Na/liq.NH3,R3:H2O,H2SO4,HgSO4,R4:(i)O3,(ii)H2O
In the first reaction (R1), hydrogen in presence of Lindlar catalyst is used. Carbon carbon tripple bond is selectively reduced to double bond. Syn addition results in cis alkene. In the second reaction (R2), sodium metal in liq ammonia is used. Anti addition results in trans alkene.
The third reaction (R3) is the hydration of alkene. 1% mercuric sulphate and dil sulphuric acid are added. The intermediate enol is tautomerized to keto. The reaction is called kucherov reaction. The fourth reaction (R4) is the ozonolysis reaction. The reagents are ozone and water. The carbon carbon tripple bond breaks to form moles of carboxylic acid.

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