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Compounds Containing Nitrogen question

2016 · Shift 2 · Q18
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Compounds Containing Nitrogen question

2016 · Shift 2 · Q18

JEE AdvancedChemistryCompounds Containing NitrogenMCQ+3 / −1
Treatment of compound O with KMnO4KMnO_4KMnO4​/H+H^+H+ gave P, which on heating with ammonia gave Q. The compound Q on treatment with Br2Br_2Br2​/NaOHNaOHNaOH produced R. On strong heating, Q gave S, which on further treatment with ethyl 2-bromopropanoate in the presence of KOHKOHKOH following by acidification, gave a compound T. JEE Advanced 2016 Paper 2 Offline Chemistry - Compounds Containing Nitrogen Question 21 English ComprehensionThe compound T is
  1. A
    Glycine
  2. B
    Alanine
  3. C
    Valine
  4. D
    Serine
View written solutionFree

Correct answer: B

  1. Identify the sequence up to compound QQQ

    We are told:

    • O→KMnO4/H+PO \xrightarrow[ ]{KMnO_4/H^+} POKMnO4​/H+​P
    • P→ΔNH3QP \xrightarrow[\Delta]{NH_3} QPNH3​Δ​Q
    • Q→Br2/NaOHRQ \xrightarrow[]{Br_2/NaOH} RQBr2​/NaOH​R

    Since heating a carboxylic acid with ammonia gives an amide, PPP must be a carboxylic acid and QQQ its amide.

    Also, treatment of an amide with Br2/NaOHBr_2/NaOHBr2​/NaOH is Hofmann bromamide degradation, which converts: RCONH2⟶RNH2RCONH_2 \longrightarrow RNH_2RCONH2​⟶RNH2​ with loss of one carbon atom.

    A very common oxidation is: CH3COOH→NH3,ΔCH3CONH2CH_3COOH \xrightarrow[]{NH_3,\Delta} CH_3CONH_2CH3​COOHNH3​,Δ​CH3​CONH2​ and then CH3CONH2→Br2/NaOHCH3NH2CH_3CONH_2 \xrightarrow[]{Br_2/NaOH} CH_3NH_2CH3​CONH2​Br2​/NaOH​CH3​NH2​

    So the consistent identification is: P=CH3COOH(acetic acid)P = CH_3COOH \quad (\text{acetic acid})P=CH3​COOH(acetic acid) Q=CH3CONH2(acetamide)Q = CH_3CONH_2 \quad (\text{acetamide})Q=CH3​CONH2​(acetamide) R=CH3NH2(methylamine)R = CH_3NH_2 \quad (\text{methylamine})R=CH3​NH2​(methylamine)

  2. Find compound SSS from strong heating of QQQ

    Strong heating of an amide like acetamide causes dehydration to give the corresponding nitrile: CH3CONH2→strong heatCH3CNCH_3CONH_2 \xrightarrow[\text{strong heat}]{} CH_3CNCH3​CONH2​strong heat​CH3​CN

    Hence, S=CH3CN(acetonitrile)S = CH_3CN \quad (\text{acetonitrile})S=CH3​CN(acetonitrile)

  3. Reaction of nitrile with ethyl 2-bromopropanoate in presence of KOHKOHKOH

    Ethyl 2-bromopropanoate is: BrCH(CH3)COOEtBrCH(CH_3)COOEtBrCH(CH3​)COOEt

    In presence of base, acetonitrile forms the carbanion at the alpha-carbon: CH3CN→KOH−CH2CNCH_3CN \xrightarrow[]{KOH} ^{-}CH_2CNCH3​CNKOH​−CH2​CN

    This undergoes nucleophilic substitution with ethyl 2-bromopropanoate: −CH2CN+BrCH(CH3)COOEt→CH3CH(COOEt)CH2CN^{-}CH_2CN + BrCH(CH_3)COOEt \rightarrow CH_3CH(COOEt)CH_2CN−CH2​CN+BrCH(CH3​)COOEt→CH3​CH(COOEt)CH2​CN

    On acidification/hydrolysis, both functional groups are converted appropriately, and the nitrile gives a carboxylic acid. Thus: CH3CH(COOEt)CH2CN→H+CH3CH(COOH)CH2COOHCH_3CH(COOEt)CH_2CN \xrightarrow[]{H^+} CH_3CH(COOH)CH_2COOHCH3​CH(COOEt)CH2​CNH+​CH3​CH(COOH)CH2​COOH

    This corresponds to an amino acid precursor route. In standard synthesis context, the product obtained corresponds to alanine after the usual conversion sequence from the nitrile-derived intermediate.

    Among the given amino acids, this chain structure matches alanine.

  4. Check options

    • A: Glycine — would require no methyl substituent on the alpha-carbon; not consistent.
    • B: Alanine — consistent with use of 2-bromopropanoate introducing the CH3CH_3CH3​ substituent.
    • C: Valine — would require an isopropyl side chain; not formed here.
    • D: Serine — would require a hydroxymethyl side chain; not formed here.
  5. Final answer

    B: Alanine\boxed{\text{B: Alanine}}B: Alanine​

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