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Alcohols Phenols and Ethers question

2007 · Shift 0 · Q18
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  5. /2007 · Shift 0 · Q18

Alcohols Phenols and Ethers question

2007 · Shift 0 · Q18

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
In the following sequence of reactions, CH3CH2OHCH_3CH_2OHCH3​CH2​OH →P+I2\xrightarrow{P + {I_2}}P+I2​​ A ⟶etherMg\mathrel{\mathop{\kern0pt\longrightarrow} \limits_{ether}^{Mg}}ether⟶Mg​ B →HCHO\xrightarrow{HCHO}HCHO​ C →H2O\xrightarrow{{H_2}O}H2​O​ D the compound ‘D’ is
  1. A
    butanal
  2. B
    n-butyl alcohol
  3. C
    n-propyl alcohol
  4. D
    propanal
View written solutionFree

Correct answer: C

  1. First reaction: ethanol with P+I2P + I_2P+I2​

    Red phosphorus and iodine generate PI3PI_3PI3​ in situ, which converts alcohols to alkyl iodides.

    3CH3CH2OH+PI3→3CH3CH2I+H3PO33CH_3CH_2OH + PI_3 \rightarrow 3CH_3CH_2I + H_3PO_33CH3​CH2​OH+PI3​→3CH3​CH2​I+H3​PO3​

    So, A=CH3CH2I(ethyl iodide)A = CH_3CH_2I \quad (\text{ethyl iodide})A=CH3​CH2​I(ethyl iodide)

  2. Second reaction: AAA with Mg in dry ether

    Alkyl iodide reacts with magnesium in dry ether to form the Grignard reagent.

    CH3CH2I+Mg→dry etherCH3CH2MgICH_3CH_2I + Mg \xrightarrow[\text{dry ether}]{} CH_3CH_2MgICH3​CH2​I+Mgdry ether​CH3​CH2​MgI

    Hence, B=C2H5MgI(ethyl magnesium iodide)B = C_2H_5MgI \quad (\text{ethyl magnesium iodide})B=C2​H5​MgI(ethyl magnesium iodide)

  3. Third reaction: Grignard reagent with formaldehyde

    Grignard reagents react with formaldehyde to give, after hydrolysis, a primary alcohol with one extra carbon.

    First addition step: CH3CH2MgI+HCHO→CH3CH2CH2OMgICH_3CH_2MgI + HCHO \rightarrow CH_3CH_2CH_2OMgICH3​CH2​MgI+HCHO→CH3​CH2​CH2​OMgI

    So, C=CH3CH2CH2OMgIC = CH_3CH_2CH_2OMgIC=CH3​CH2​CH2​OMgI

  4. Fourth reaction: hydrolysis

    On hydrolysis: CH3CH2CH2OMgI+H2O→CH3CH2CH2OH+Mg(OH)ICH_3CH_2CH_2OMgI + H_2O \rightarrow CH_3CH_2CH_2OH + Mg(OH)ICH3​CH2​CH2​OMgI+H2​O→CH3​CH2​CH2​OH+Mg(OH)I

    Therefore, D=CH3CH2CH2OHD = CH_3CH_2CH_2OHD=CH3​CH2​CH2​OH

    This is n-propyl alcohol.

  5. Check options

    • A: butanal →\to→ incorrect
    • B: n-butyl alcohol →\to→ incorrect
    • C: n-propyl alcohol →\to→ correct
    • D: propanal →\to→ incorrect

Thus, the final compound DDD is n-propyl alcohol.

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