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An organic compound (A) with molecular f...

An organic compound (A) with molecular formula `C_(7)H_(8)O` dissolves in NaOH and gives characteristic colour with `FeCl_(3)`. On treatement with `Br_(3)`, it gives a tribromo product `C_(7)H_(5)Br_(3)`. The compound is:

A

p-Hydroxybenzene

B

2-Methoxy-2-phenyl propane

C

m-Cresol

D

p-Cresol

Text Solution

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The correct Answer is:
To solve the question regarding the organic compound (A) with the molecular formula C₇H₈O, we will follow these steps: ### Step 1: Determine the Degree of Unsaturation The degree of unsaturation (DU) can be calculated using the formula: \[ \text{DU} = \frac{2C + 2 - H}{2} \] where C is the number of carbon atoms and H is the number of hydrogen atoms. For the compound C₇H₈O: - C = 7 - H = 8 Substituting the values: \[ \text{DU} = \frac{2(7) + 2 - 8}{2} = \frac{14 + 2 - 8}{2} = \frac{8}{2} = 4 \] ### Step 2: Analyze the Structure A degree of unsaturation of 4 suggests the presence of a benzene ring (which accounts for 4 degrees of unsaturation). This indicates that the compound likely has a benzene ring and may also have additional substituents. ### Step 3: Identify Functional Groups The presence of an -OH group (hydroxyl group) is indicated by the molecular formula C₇H₈O. Given that the compound dissolves in NaOH and gives a characteristic color with FeCl₃, this suggests that the compound is a phenol. ### Step 4: Consider Substituents on the Benzene Ring Since the compound gives a tribromo product (C₇H₅Br₃) upon treatment with Br₂, this indicates that bromine is adding to the benzene ring. The formation of a tribromo product suggests that both ortho and para positions on the ring are available for substitution, which implies that a methyl group (–CH₃) is likely present at the meta position relative to the hydroxyl group. ### Step 5: Identify the Compound Considering the structure we have deduced: - The compound is a phenol (due to the -OH group). - The methyl group is at the meta position relative to the -OH group. This compound is known as **meta-cresol** or **metacresol**. ### Conclusion The organic compound (A) is **metacresol**.

To solve the question regarding the organic compound (A) with the molecular formula C₇H₈O, we will follow these steps: ### Step 1: Determine the Degree of Unsaturation The degree of unsaturation (DU) can be calculated using the formula: \[ \text{DU} = \frac{2C + 2 - H}{2} \] where C is the number of carbon atoms and H is the number of hydrogen atoms. For the compound C₇H₈O: ...
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Explore conceptually related problems

An organic compound (A) with molecular formula C_(7)H_(8)O dissolves in NaOH and gives characteristic colour with FeCl_(3) . On treatment with Br_(2) , it gives a tribromo product C_(7)H_(5)OBr_(3) . The compound is:

Compound (A) C_(7)H_(8)O is insoluble in aqueous NaHCO_(3) and dissolves in aqueous NaOH and gives a characteristic colour with neutral FeCl_(3) . When treated with Br_(2) (A) forms compound (B) C_(7)H_(5)O Br_(3) . The most probable structure of compound A is :

Knowledge Check

  • Compound (A) C_(7)H_(8)O is insoluble in aqueous NaHCO_(3) and dissolves in aqueous NaOH and gives a characteristic colour with neutral FeCl_(3) . When treated with Br_(2) (A) forms compound (B) C_(7)H_(5)OBr_(3) . The most probable structure of compound A is :

    A
    B
    C
    D
  • Compound (A) C_(7)H_(8)O is insoluble in aqueous NaHCO_(3) and dissolves in aqueous NaOH and gives a characteristic colour with neutral FeCl_(3) . When treated with Br_(2) (A) forms compound (B) C_(7)H_(5)OBr_(3) . The structure of compound (B) would be :

    A
    B
    C
    D
  • Compound (A) C_(7)H_(8)O is insoluble in aqueous NaHCO_(3) and dissolves in aqueous NaOH and gives a characteristic colour with neutral FeCl_(3) . When treated with Br_(2) (A) forms compound (B) C_(7)H_(5)OBr_(3) . What could be the structure of compound (A) if neither dissolves in aq. NaHCO_(3) nor gives a characteristic colour with FeCl_(3) ?

    A
    B
    C
    D
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