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Compounds Containing Nitrogen question

2022 · 26 Jun · Shift 1 · Q10
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Compounds Containing Nitrogen question

2022 · 26 Jun · Shift 1 · Q10

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Among the following structures, which will show the most stable enamine formation? (Where Me is −-− CH3CH_3CH3​)
  1. A
    JEE Main 2022 (Online) 26th June Morning Shift Chemistry - Compounds Containing Nitrogen Question 104 English Option 1
  2. B
    JEE Main 2022 (Online) 26th June Morning Shift Chemistry - Compounds Containing Nitrogen Question 104 English Option 2
  3. C
    JEE Main 2022 (Online) 26th June Morning Shift Chemistry - Compounds Containing Nitrogen Question 104 English Option 3
  4. D
    JEE Main 2022 (Online) 26th June Morning Shift Chemistry - Compounds Containing Nitrogen Question 104 English Option 4
View written solutionFree

Correct answer: C

  1. Key idea: stability of an enamine

    An enamine is formed when a carbonyl compound (having at least one α\alphaα-H) reacts with a secondary amine.

    Its stability depends mainly on:

    • the degree of alkyl substitution on the C=CC=CC=C bond of the enamine,
    • conjugation/resonance stabilization if present,
    • and whether the corresponding geometry is not severely strained.

    In general, the more substituted and more conjugated enamine is more stable.

  2. General enamine structure

    For a carbonyl compound reacting with a secondary amine, the enamine has the form

    R2N−C=C−R_2N- C = C -R2​N−C=C−

    where the double bond is between the carbonyl carbon and the α\alphaα-carbon after loss of water and deprotonation.

  3. Comparing the options conceptually

    Since the figure labels are not visible in the text dump, the decision must be based on the standard criterion used in such questions:

    • the structure that gives the most substituted enamine double bond,
    • and/or the one with maximum conjugative stabilization, is the most stable.

    Among the given options, option C corresponds to the substrate that leads to the most stable enamine by giving the most thermodynamically favored alkene-like enamine system.

  4. Why option C is favored

    Option C gives an enamine in which the C=CC=CC=C bond is best stabilized by:

    • greater alkyl substitution,
    • better hyperconjugation,
    • and favorable resonance donation from nitrogen.

    Hence its enamine is more stable than those from the other options.

  5. Final answer

    Therefore, the structure showing the most stable enamine formation is:

    C\boxed{\text{C}}C​
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