Alcohols and Ethers - Result Question 6

####9. Which is the most suitable reagent for the following transformation?

(2019 Main, 10 Jan II)

CH3CH=CHCH2CO2H

(a) Tollen’s reagent

(b) I2/NaOH

(c) Alkaline KMnO4

(d) CrO2Cl2/CS2

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Answer:

Correct Answer: 9. (b)

Solution:

  1. The most suitable reagent to carry out given transformation is I2/NaOH

CH36C5H=C4HC3H2C2OHC1H3 (Oxidative cleavage)  Strong oxidation, [O]

CH36C5H=C4HCH23C2OH

Here, the haloform reaction will give following reaction:

(i) Tollen’s reagent (AgNO3+NH4OH) is a mild oxidising agent. It does not react with CHCH3 group

(2-alcohol).

(ii) Alkaline KMnO4 cannot perform the oxidative cleavage, rather it will hydroxylate the C=C.

(iv) CrO2Cl2/CS2 will not react here.



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