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An organic compound (A) C(8)H(10)O was ...

An organic compound (A) `C_(8)H_(10)O` was subjected to a series of test in laboratory. It was found that this compound :
(i) Rotates the plane polarized light
(ii) Evolves `H_(2)` gas with Na.
(iii)Reacts with `I_(2)` and NaOH to produce yellow ppt.
(iv) Does not react with `Br_(2)//"CC"l_(4)`
(v) Reats wtih not `KMnO_(4)` to form `(B)C_(7)H_(6)O_(2)`, which can also be synthesized by benzene and carbonyl chloride followed by hydrolysis.
(vi) Loses optical activity as a result of reduction with Res P+HI to form 'C'
(vii) Reacts with Lucas reagent in about 5 minutes.
Compounds B and C are respectively :

A

B

C

D

Text Solution

Verified by Experts

The correct Answer is:
C
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An organic compound (A) C_(8)H_(10)O was subjected to a series of test in laboratory. It was found that this compound : (i) Rotates the plane polarized light (ii) Evolves H_(2) gas with Na. (iii)Reacts with I_(2) and NaOH to produce yellow ppt. (iv) Does not react with Br_(2)//"CC"l_(4) (v) Reats wtih not KMnO_(4) to form (B)C_(7)H_(6)O_(2) , which can also be synthesized by benzene and carbonyl chloride followed by hydrolysis. (vi) Loses optical activity as a result of reduction with Res P+HI to form 'C' (vii) Reacts with Lucas reagent in about 5 minutes. Find out structure of compound 'A' :

An organic compound (A) C_(8)H_(10)O was subjected to a series of test in laboratory. It was found that this compound : (i) Rotates the plane polarized light (ii) Evolves H_(2) gas with Na. (iii)Reacts with I_(2) and NaOH to produce yellow ppt. (iv) Does not react with Br_(2)//"CC"l_(4) (v) Reats wtih not KMnO_(4) to form (B)C_(7)H_(6)O_(2) , which can also be synthesized by benzene and carbonyl chloride followed by hydrolysis. (vi) Loses optical activity as a result of reduction with Res P+HI to form 'C' (vii) Reacts with Lucas reagent in about 5 minutes. A overset("TsCl")rarr X overset("alc. KOH")rarr Y overset("conc." H_(2)SO_(4))rarr Z . Find out correct structure of Z.