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Organic Chemistry – Some Basic Principles And Techniques

Question
CBSEENCH11007625

How will you test the presence of halogen in an organic compound by Lassaigne's test?

Solution

Lassaigne's test:
This test involves following two steps;
1. Preparation of Lassaigne's or sodium extract:
     Na space plus space space straight X with From space organic space compound below space space rightwards arrow space space space space NaX with Sodium space halide below
where X may be Cl, Br or I.
2. Test for halogen: The Lassaigne’s filtrate is boiled with concentrated nitric acid, cooled and then treated with silver nitrate solution. Formation of precipitate indicates the presence of halogen.
(i) White precipitate soluble in ammonium hydroxide indicates the presence of chlorine in the compound then treated with silver nitrate solution. Formation of precipitate indicates the presence of halogen.
Na space plus space Cl with left parenthesis from space organic space compound right parenthesis below space space space rightwards arrow with Fusion on top space space space NaCl
NaCl space plus space AgNO subscript 3 space space rightwards arrow space space space space AgCl with White space ppt. below space plus space space NaNO subscript 3
AgCl space plus space 2 NH subscript 4 OH space space rightwards arrow space space stack space left square bracket Ag left parenthesis NH subscript 3 right parenthesis subscript 2 Cl with Diammine space siler space chloride below space plus space 2 straight H subscript 2 straight O
(ii) Light yellow precipitate partially soluble in ammonium hydroxide indicates the presence of bromine in the organic compound.
  Na space plus space Br with From space organic space compound below space space rightwards arrow with Fusion on top space NaBr
NaBr space plus space AgNO subscript 3 space rightwards arrow space space space AgBr with Light space yellow space ppt. below space plus space NaNO subscript 3
(iii) Bright yellow precipitate insoluble in ammonium hydroxide indicates the presence of iodine in the compound. 
    Na space plus space straight I with From space organic space compound below space space space rightwards arrow with Fusion on top space space space NaI
NaI space plus space AgNO subscript 3 space rightwards arrow space space AgI with Bright space yellow space ppt. space below space plus space NaNO subscript 3