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Question

A terpene has molecular formula A(C10H16O) and it is a major constituent of lemongrass oil. A on treatment with acidified KMnO4 solution produces acetone, Oxalic acid and CH3COCH2CH2COOH. Also, A does not give silver mirror test with Tollen's reagent. The correct deduction regarding A is/are :

A
A gives positive iodoform test
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B
A has two stereoismers
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C
A has one chiral carbon
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D
A on treatment with NH2OH gives six pair of diastereomers.
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Solution

The correct option is A A gives positive iodoform test
The structure of the terpene (A) is as shown. It has molecular formula C10H16O
A on treatment with acidified KMnO4
solution produces acetone (CH3COCH3), Oxalic acid (HCOOHCOOH) and
CH3COCH2CH2COOH.
Also, A does not give silver mirror test with Tollen's reagent as it does not contain an aldehyde group. A gives positive iodoform test as it contains a methyl keto group. Hence, the option (A) is the correct answer.
516466_208072_ans.png

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