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Question

Chemistry Question on Organic Reactions

In the above chemical reaction sequence “A’’ and “B” respectively are :

A

O3,Zn/H2OandNaOH(alc.)/I2\text{O}_3, \, \text{Zn}/\text{H}_2\text{O} \, \text{and} \, \text{NaOH}_{(\text{alc.})}/\text{I}_2

B

H2O,H+andNaOH(alc.)/I2\text{H}_2\text{O}, \, \text{H}^+ \, \text{and} \, \text{NaOH}_{(\text{alc.})}/\text{I}_2

C

H2O,H+andKMnO4\text{H}_2\text{O}, \, \text{H}^+ \, \text{and} \, \text{KMnO}_4

D

O3,Zn/H2OandKMnO4\text{O}_3, \, \text{Zn}/\text{H}_2\text{O} \, \text{and} \, \text{KMnO}_4

Answer

O3,Zn/H2OandNaOH(alc.)/I2\text{O}_3, \, \text{Zn}/\text{H}_2\text{O} \, \text{and} \, \text{NaOH}_{(\text{alc.})}/\text{I}_2

Explanation

Solution

Explanation 65
Step 1: Ozonolysis (formation of compound A):} The double bond in the cycloalkene undergoes ozonolysis in the presence of ozone (O3\text{O}_3) followed by reduction with Zn/H2O\text{H}_2\text{O}. This cleaves the double bond, producing two aldehyde groups on adjacent carbons. 2.
Step 2: Haloform reaction (formation of compound B): The aldehyde (or ketone) group in compound A reacts with NaOH(alc)\text{NaOH}_{(\text{alc})} and I2\text{I}_2 (haloform reaction). This cleaves the terminal methyl ketone or aldehyde group to produce sodium formate (HCOONa\text{HCOONa}) and iodoform (CHI3\text{CHI}_3), leaving a carboxylic acid group. The final product, compound B, contains a carboxylate ion (COO\text{COO}^-) and a secondary alcohol group. The complete reaction mechanism ensures the correct conversion of "A" to "B."