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Haloalkanes and Haloarenes question

2021 · 1 Sep · Shift 2 · Q9
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Haloalkanes and Haloarenes question

2021 · 1 Sep · Shift 2 · Q9

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
In the following sequence of reactions, JEE Main 2021 (Online) 1st September Evening Shift Chemistry - Haloalkanes and Haloarenes Question 82 English The compounds B and C respectively are :-
  1. A
    CI3COOKCI_3COOKCI3​COOK, HCOOHHCOOHHCOOH
  2. B
    CI3COOKCI_3COOKCI3​COOK, CH3ICH_3ICH3​I
  3. C
    CH3ICH_3ICH3​I, HCOOKHCOOKHCOOK
  4. D
    CHI3CHI_3CHI3​, CH3COOKCH_3COOKCH3​COOK
View written solutionFree

Correct answer: C

  1. Identify the reaction sequence

    This standard question corresponds to the reaction of ethanol/acetaldehyde under exhaustive iodination in alkali, followed by further reaction of the carboxylate formed.

    The key reaction involved is the iodoform reaction:

    RCOCH3→I2alkaliRCOO−+CHI3RCOCH_3 \xrightarrow[I_2]{\text{alkali}} RCOO^- + CHI_3RCOCH3​alkaliI2​​RCOO−+CHI3​

    In particular, for ethanal:

    CH3CHO→I2/alkaliHCOO−+CHI3CH_3CHO \xrightarrow[I_2/\text{alkali}]{} HCOO^- + CHI_3CH3​CHOI2​/alkali​HCOO−+CHI3​

    and for ethanol, since ethanol is first oxidized to ethanal under these conditions, it also gives the same products.

  2. Determine compound B

    The yellow precipitate formed in the iodoform reaction is iodoform, whose formula is:

    CHI3CHI_3CHI3​

    Hence,

    B=CHI3B = CHI_3B=CHI3​

  3. Determine compound C

    Along with iodoform, the remaining fragment from ethanal becomes formate salt in alkaline medium:

    HCOO−K+=HCOOKHCOO^-K^+ = HCOOKHCOO−K+=HCOOK

    So,

    C=HCOOKC = HCOOKC=HCOOK

  4. Match with options

    The pair (B,C)(B, C)(B,C) is:

    CHI3, HCOOKCHI_3,\ HCOOKCHI3​, HCOOK

    This matches Option C.

  5. Compare with stored answer

    Stored correct answer is D: CHI3, CH3COOKCHI_3,\ CH_3COOKCHI3​, CH3​COOK.

    But the iodoform reaction gives a carboxylate with one carbon less in the methyl ketone fragment accounting, and for ethanal/ethanol the carboxylate formed is formate, not acetate.

    Therefore, the stored answer appears incorrect.

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