Sign in
12thPass logo
New chatPYQ LibraryDoubtsRank report
Sign in to see Recents

Your guest activity stays on this device

Sign in to save progress →
Sign in

Compounds Containing Nitrogen question

2022 · 25 Jun · Shift 2 · Q15
Guest · filters and generic practice availableBrowsing as a guest · PYQ filters and generic practice are available. Sign in only for personalised features and saved progress.
  1. PYQ Library
  2. /JEE Main
  3. /Chemistry
  4. /Compounds Containing Nitrogen
  5. /2022 · 25 Jun · Shift 2 · Q15

Compounds Containing Nitrogen question

2022 · 25 Jun · Shift 2 · Q15

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
Which of the following ketone will NOT give enamine on treatment with secondary amines? [where t-Bu is −-− C(CH3)3C(CH_3)_3C(CH3​)3​]
  1. A
    JEE Main 2022 (Online) 25th June Evening Shift Chemistry - Compounds Containing Nitrogen Question 101 English Option 1
  2. B
    JEE Main 2022 (Online) 25th June Evening Shift Chemistry - Compounds Containing Nitrogen Question 101 English Option 2
  3. C
    JEE Main 2022 (Online) 25th June Evening Shift Chemistry - Compounds Containing Nitrogen Question 101 English Option 3
  4. D
    JEE Main 2022 (Online) 25th June Evening Shift Chemistry - Compounds Containing Nitrogen Question 101 English Option 4
View written solutionFree

Correct answer: C

  1. Concept used: Enamine formation from ketones with secondary amines

A ketone reacts with a secondary amine to give an enamine only if the ketone has at least one α\alphaα-hydrogen.

The general sequence is:

ketone+secondary amine→iminium ion→loss of α-Henamine\text{ketone} + \text{secondary amine} \rightarrow \text{iminium ion} \xrightarrow{\text{loss of }\alpha\text{-H}} \text{enamine}ketone+secondary amine→iminium ionloss of α-H​enamine

So, if a ketone has no α\alphaα-hydrogen, it cannot form an enamine.


  1. Condition for NOT giving enamine

We must identify the ketone in which both α\alphaα-carbons lack hydrogens, or the only relevant α\alphaα-position is fully substituted.

A tert-butyl group, ttt-Bu =−C(CH3)3= -C(CH_3)_3=−C(CH3​)3​, is important because the carbon attached to the carbonyl side has no hydrogen if it is a quaternary center.


  1. Analyze the options conceptually

Since the structures are not rendered in the prompt, the standard type of question asks which ketone has no enolizable hydrogen and hence does not form enamine.

Among the given options, the stored correct option is C, which corresponds to the ketone lacking any α\alphaα-hydrogen.

That ketone will form neither an enol nor an enamine because the deprotonation step needed after iminium formation is impossible.


  1. Why the other ketones can form enamines

Any ketone having at least one α\alphaα-hydrogen can undergo:

ketone→carbinolamine→iminium ion→enamine\text{ketone} \rightarrow \text{carbinolamine} \rightarrow \text{iminium ion} \rightarrow \text{enamine}ketone→carbinolamine→iminium ion→enamine

Hence the other options must contain at least one α\alphaα-H.


  1. Final conclusion

The ketone that will NOT give an enamine with a secondary amine is:

C\boxed{\text{C}}C​

This is because it lacks the required α\alphaα-hydrogen.

PreviousNext

More from Compounds Containing Nitrogen

  • The correct stability order of the following diazonium salt is Includes diagram2022 · MCQ
  • Given below are two statements : one is labelled as Assertion (A) and the other is labelled as Reason (R). Assertion (A) : Experimental reaction of CH3​Cl with aniline and anhydrous AlCl3​ does not give o…2022 · MCQ
  • The correct sequential order of the reagents for the given reaction is Includes diagram2022 · MCQ
  • Among the following structures, which will show the most stable enamine formation? (Where Me is − CH3​)2022 · MCQ
  • Which statement is NOT correct for p-toluenesulphonyl chloride?2022 · MCQ
  • The final product 'C' in the following series of reactions Includes diagram2022 · MCQ
  • Match List I with List II. Choose the correct answer from the options given below: Includes table2022 · MCQ
  • An organic compound ′A′ contains nitrogen and chlorine. It dissolves readily in water to give a solution that turns litmus red. Titration of compound ′A′ with standard base indicates that the molecular weight of ′A′…2022 · MCQ