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The compound C8H9Cl(A) on treatments wit...

The compound `C_8H_9Cl(A)` on treatments with KCN followed by hydrolysis gives `C_9H_10O_2(B)`.Ammonium salt of B on dry distillation yields C.Which reacts with alkaline solution of bromine to gives `C_8H_11N`.(D),Another compound E `(C_6H_10O)` is obtained by the action of nitrous acid on D. or by the action of aquouspotash on A,E on oxidation gives `F(C_8H_10O)` Which gives the inner anhydride G on heating.
The compound D is reaction with `CHCl_3+NaOH` gives a compound H.The structure of H.

A

B

C

D

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To solve the problem step-by-step, we will analyze the transformations of the compounds mentioned in the question. ### Step 1: Identify Compound A The compound A is given as `C_8H_9Cl`. This suggests that it is likely an aromatic compound with a chlorine substituent. A possible structure could be chlorobenzene with a side chain, such as `C6H5-CH2Cl` (benzyl chloride). ### Step 2: Reaction of A with KCN When compound A is treated with KCN, a nucleophilic substitution occurs where the chlorine atom is replaced by a cyanide group. This results in the formation of a compound with the formula `C_8H_9CN`. ### Step 3: Hydrolysis of the Cyanide Upon hydrolysis of the cyanide (`C_8H_9CN`), it converts to a carboxylic acid. The resulting compound B will have the formula `C_9H_{10}O_2`, which can be represented as `C6H5-CH2-COOH` (benzoic acid derivative). ### Step 4: Ammonium Salt of B The ammonium salt of B can be formed by reacting B with ammonia. This results in the formation of an amide, which we will denote as compound C. ### Step 5: Dry Distillation of Ammonium Salt When the ammonium salt of B is subjected to dry distillation, it yields compound C. The structure of C is likely a simple amide derived from B. ### Step 6: Reaction of C with Alkaline Bromine Compound C reacts with an alkaline solution of bromine (Hofmann degradation), resulting in the formation of an amine, which we denote as D. The formula for D is `C_8H_{11}N`. ### Step 7: Reaction of D with Nitrous Acid When compound D reacts with nitrous acid (HNO2), it undergoes a reaction that replaces the amine group with a hydroxyl group, yielding compound E (`C_6H_{10}O`). ### Step 8: Oxidation of E Compound E is then oxidized to form compound F, which has the formula `C_8H_{10}O`. This compound can be represented as a dicarboxylic acid. ### Step 9: Heating F to Form Anhydride G Upon heating compound F, it forms an inner anhydride G. This is a cyclic structure formed from the carboxylic acid groups. ### Step 10: Reaction of D with CHCl3 and NaOH Finally, compound D reacts with CHCl3 and NaOH, which is known as the carbylamine reaction. This reaction converts the primary amine into an isocyanide (compound H). ### Summary of Compounds - **A**: `C_8H_9Cl` (Benzyl chloride) - **B**: `C_9H_{10}O_2` (Carboxylic acid) - **C**: Amide derived from B - **D**: `C_8H_{11}N` (Amine) - **E**: `C_6H_{10}O` (Alcohol) - **F**: `C_8H_{10}O` (Dicarboxylic acid) - **G**: Inner anhydride formed from F - **H**: Isocyanide formed from D

To solve the problem step-by-step, we will analyze the transformations of the compounds mentioned in the question. ### Step 1: Identify Compound A The compound A is given as `C_8H_9Cl`. This suggests that it is likely an aromatic compound with a chlorine substituent. A possible structure could be chlorobenzene with a side chain, such as `C6H5-CH2Cl` (benzyl chloride). ### Step 2: Reaction of A with KCN When compound A is treated with KCN, a nucleophilic substitution occurs where the chlorine atom is replaced by a cyanide group. This results in the formation of a compound with the formula `C_8H_9CN`. ...
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The compound C_8H_9Cl(A) on treatments with KCN followed by hydrolysis gives C_9H_10O_2(B) .Ammonium salt of B on dry distillation yields C.Which reacts with alkaline solution of bromine to gives C_8H_11N .(D),Another compound E (C_6H_10O) is obtained by the action of nitrous acid on D. or by the action of aquouspotash on A,E on oxidation gives F(C_8H_10O) Which gives the inner anhydride G on heating. The compound D is reaction with CHCl_3+NaOH gives a compound H. The compound A on reaction with AgCN gives :

The compound C_8H_9Cl(A) on treatments with KCN followed by hydrolysis gives C_9H_10O_2(B) .Ammonium salt of B on dry distillation yields C.Which reacts with alkaline solution of bromine to gives C_8H_11N .(D)Another compound E is obtained by the action of nitrous acid on D. E on oxidation gives F which gives the inner anhydride G on heating. The Compound A is :

Knowledge Check

  • Compound (A) C_8H_6O_2 on treatment with aq. NaOH followed by acidification gives (B) C_3H_2O_3 which on oxidation gives benzoic acid only:

    A
    B
    C
    D
  • A compound (A) C_(5)H_(10) Cl_(2) on hydrolysis gives C_(5)H_(10)O which reacts with NH_(2)OH , forms iodoform but does not give Fehling test (A) is :

    A
    `H_(3)C-overset(CI)overset(|)underset(CI)underset(|)C-CH_(2)CH_(2)CH_(3)`
    B
    `CH_(3)CH_(2)- overset(CI) overset(|) underset(CI)underset(|)C- CH_(2)CH_(3) `
    C
    `overset(CI)overset(|) underset(CI)underset(|) CHCH_(2) CH_(2)CH_(2)CH_(3)`
    D
    `CH_(3)CH_(2) overset(CI)overset(|)CH- overset(CI)overset(|)CHCH_(3)`
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