How will you differentiate between the following? Give a chemical test.
(i) Formaldehyde and chlorobenzene
(ii) Benzaldehyde and Benzoic acid.

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Solution

$(i)$ There is no reaction between formaldehyde and concentrated $H_{2} S O_{4}$ , however chlorobenzene reacts readily with $H_{2} S O_{4}$ (Sulphuric acid) to form chlorobenzene sulfonic acids. Refer to the above image.
$(i i)$ Test- $1$ : Through sodium bicarbonate $(N a H C O_{3})$ benzaldehyde does not react with sodium bicarbonate. However benzoic acid will produce brisk effervenscene on reaction with Sodium bicarbon as shown-
$C_{6} H_{5} C O O H + N a H C O_{3} ⟶ C_{6} H_{5} C O O N a + H_{2} O + C O_{2}$

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Give simple chemical tests to distinguish between the following pairs of compounds.

(i) Propanal and Propanone

(ii) Acetophenone and Benzophenone

(iii) Phenol and Benzoic acid

(iv) Benzoic acid and Ethyl benzoate

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2 C_{6} H_{5} C H O + C o n c . N a O H ⟶

C H_{3} C O O H {C l}_{2} / P - ------ \to

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