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Question

A hydrocarbon X(C7H14) on ozonolysis followed by work-up Zn−H2O gives C6H12O as one of the product which on subsequent treatment with KOH/I2 gives yellow precipitate and salt of a chiral acid. Hence, X could be

A
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B
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C
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D
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Solution

The correct option is B
Ozonolysis of X(C7H14) gives C6H12O which has one carbon less than X. Thus, X must contain double bond at terminal carbon.

Iodoform test: When Iodine and potassium hydroxide are added to a compound that contains either a methyl ketone or a secondary alcohol with a methyl group in the alpha position, a pale yellow precipitate of iodoform or triiodomethane is formed.
Iodoform test is used to check the presence of carbonyl compounds with the structure RCOCH3 or alcohols with the structure RCH(OH)CH3 in a given unknown substance.
If an aldehyde gives a positive iodoform test, then it must be acetaldehyde since it is the only aldehyde with a CH3C=O group.
C6H12O is a ketone with the structure RCOCH3 which gives iodoform test as shown in the reaction.
Hence option (b) is correct.


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