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Aldehydes Ketones and Carboxylic Acids question

2003 · Shift 0 · Q26
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Aldehydes Ketones and Carboxylic Acids question

2003 · Shift 0 · Q26

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
The reaction of chloroform with alcoholic KOHKOHKOH and p-toluidine forms
  1. A
    AIEEE 2003 Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 222 English Option 1
  2. B
    AIEEE 2003 Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 222 English Option 2
  3. C
    AIEEE 2003 Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 222 English Option 3
  4. D
    AIEEE 2003 Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 222 English Option 4
View written solutionFree

Correct answer: C

  1. Identify the reaction type

    Chloroform, CHCl3\mathrm{CHCl_3}CHCl3​, when treated with alcoholic KOH\mathrm{KOH}KOH, generates dichlorocarbene, :CCl2: \mathrm{CCl_2}:CCl2​.

    CHCl3+KOH→:CCl2+KCl+H2O\mathrm{CHCl_3 + KOH \rightarrow :CCl_2 + KCl + H_2O}CHCl3​+KOH→:CCl2​+KCl+H2​O

  2. Reaction of primary amine with chloroform and alcoholic KOH

    ppp-Toluidine is a primary aromatic amine:

    p-toluidine=p-methyl aniline=p-CH3C6H4NH2p\text{-toluidine} = p\text{-methyl aniline} = \mathrm{p\text{-}CH_3C_6H_4NH_2}p-toluidine=p-methyl aniline=p-CH3​C6​H4​NH2​

    A primary amine reacts with chloroform and alcoholic KOH\mathrm{KOH}KOH in the carbylamine reaction to form an isocyanide (isonitrile).

    General reaction:

    RNH2+CHCl3+3KOH→RNC+3KCl+3H2O\mathrm{RNH_2 + CHCl_3 + 3KOH \rightarrow RNC + 3KCl + 3H_2O}RNH2​+CHCl3​+3KOH→RNC+3KCl+3H2​O

  3. Apply to ppp-toluidine

    Here, R=p-CH3C6H4\mathrm{R = p\text{-}CH_3C_6H_4}R=p-CH3​C6​H4​. Therefore:

    p-CH3C6H4NH2+CHCl3+3KOH\mathrm{p\text{-}CH_3C_6H_4NH_2 + CHCl_3 + 3KOH}p-CH3​C6​H4​NH2​+CHCl3​+3KOH →p-CH3C6H4NC+3KCl+3H2O\mathrm{\rightarrow p\text{-}CH_3C_6H_4NC + 3KCl + 3H_2O}→p-CH3​C6​H4​NC+3KCl+3H2​O

    So the product formed is ppp-tolyl isocyanide (or ppp-methyl phenyl isocyanide).

  4. Conclusion

    The reaction gives an isocyanide as the final product.

    Since the stored correct answer is C, the correct option must correspond to ppp-tolyl isocyanide.

p-CH3C6H4NC\boxed{\mathrm{p\text{-}CH_3C_6H_4NC}}p-CH3​C6​H4​NC​

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