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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 aromatic compound (A), C_(9)H_(12)O was subjeted to a series of tests in the laboratory. It was found that this compound , (i) does not form silver mirror with Tollens' reagent. (ii) rotates the plane of polarised light. (iii) reacts with sodium metal to evolve hydrogen gas. ltbr. (iv) does not decolourise pink colour of bromine water. (v) reacts with hot KMnO_(4) to form monocarboxylic acid 'B' which on decarboxylation gives benzene. (vi) reacts with Lucas reagent in about 5 min. (vii) reacts with I_(2) and NaOH to produce yellow coloured precipitation of the compound (C ) . (viii) loses its optical activity due to formation of compound (D ) on reaction with Red P and HI. The functional groups present in the compound (A) is :

An aromatic compound (A), C_(9)H_(12)O was subjeted to a series of tests in the laboratory. It was found that this compound , (i) does not form silver mirror with Tollens' reagent. (ii) rotates the plane of polarised light. (iii) reacts with sodium metal to evolve hydrogen gas. ltbr. (iv) does not decolourise pink colour of bromine water. (v) reacts with hot KMnO_(4) to form monocarboxylic acid 'B' which on decarboxylation gives benzene. (vi) reacts with Lucas reagent in about 5 min. (vii) reacts with I_(2) and NaOH to produce yellow coloured precipitation of the compound (C ) . (viii) loses its optical activity due to formation of compound (D ) on reaction with Red P and HI. Structure of the compound (A ) will be :

Knowledge Check

  • 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' :

    A
    B
    C
    D

  • 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.

    A
    B
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  • An aromatic compound (A), C_(9)H_(12)O was subjeted to a series of tests in the laboratory. It was found that this compound , (i) does not form silver mirror with Tollens' reagent. (ii) rotates the plane of polarised light. (iii) reacts with sodium metal to evolve hydrogen gas. ltbr. (iv) does not decolourise pink colour of bromine water. (v) reacts with hot KMnO_(4) to form monocarboxylic acid 'B' which on decarboxylation gives benzene. (vi) reacts with Lucas reagent in about 5 min. (vii) reacts with I_(2) and NaOH to produce yellow coloured precipitation of the compound (C ) . (viii) loses its optical activity due to formation of compound (D ) on reaction with Red P and HI. Molecular formula of the compound (C ) will be :

    A
    `CH_(3)I`
    B
    C
    `CHI_(3)`
    D

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