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Saturday, 31 October

JEE Main 2023 · ChemistryMultiple choiceOtherMediumMulti-step

JEE Main 10 April 2023, Shift 1, Chemistry Q76

Question 76 of 90 in this shift, Chemistry question 16 of 30, Section A. NTA dropped this question from the final key; it is left out of every count on this site.

Isomeric amines with molecular formula C8H11N\mathrm{C_8H_{11}N} give the following tests Isomer (P) ⇒\Rightarrow Can be prepared by Gabriel phthalimide synthesis Isomer (Q) ⇒\Rightarrow Reacts with Hinsberg’s reagent to give solid insoluble in NaOH Isomer (R) ⇒\Rightarrow Reacts with HONO followed by β\beta – naphthol in NaOH to give red dye. Isomers (P), (Q) and (R) respectively are

The figure, in words

Each option shows three skeletal structures labelled by column P, Q, R.
  1. (1)P: [figure: C6H5CH2NHCH3\mathrm{C_6H_5CH_2NHCH_3} (benzyl attached to NHCH3)]; Q: [figure: C6H5CH2CH2NH2\mathrm{C_6H_5CH_2CH_2NH_2}]; R: [figure: benzene ring with CH3\mathrm{CH_3} ortho to CH2−NH2\mathrm{CH_2{-}NH_2} (drawn as N–H with H below), i.e. 2-methylbenzylamine]
  2. (2)P: [figure: C6H5CH2CH2NH2\mathrm{C_6H_5CH_2CH_2NH_2}]; Q: [figure: benzene ring with CH2−N(H)−CH3\mathrm{CH_2{-}N(H){-}CH_3} and an ortho CH3\mathrm{CH_3} (drawn as N–H with CH3\mathrm{CH_3} below, and ring CH3\mathrm{CH_3})]; R: [figure: 4-ethylaniline, NH2\mathrm{NH_2} para to ethyl]
  3. (3)P: [figure: 2-ethylaniline, NH2\mathrm{NH_2} ortho to ethyl]; Q: [figure: C6H5CH2CH2NH2\mathrm{C_6H_5CH_2CH_2NH_2}]; R: [figure: N-ethylaniline, C6H5NH−CH2CH3\mathrm{C_6H_5NH{-}CH_2CH_3}]
  4. (4)P: [figure: C6H5CH2CH2NH2\mathrm{C_6H_5CH_2CH_2NH_2}]; Q: [figure: N,N-dimethylaniline, C6H5N(CH3)2\mathrm{C_6H_5N(CH_3)_2}]; R: [figure: 2-ethylaniline, NH2\mathrm{NH_2} ortho to ethyl]

Official answer

Dropped by NTA (marks given to all)

NTA final key: NTA final key: DROP (question dropped).

Chapter
Amines
Topic
Amines
Idea tested
Hinsberg Test

Same idea in other shifts

Asked 13× in all
  1. 8 Apr 2024, Shift 1 · Q90Number of amine compounds from the following giving solids which are soluble in NaOH upon reaction with Hinsberg's reagent is __________.…MediumNumerical valueHas a figure
  2. 8 Apr 2024, Shift 2 · Q79Given below are two statements : Statement (I) : All the following compounds react with p-toluenesulfonyl chloride. C6H5NH2\mathrm{C_6H_5NH_2}…MediumTwo statements
  3. 1 Feb 2024, Shift 2 · Q89Number of compounds which give reaction with Hinsberg's reagent is ________. [figure: eleven structures in three rows]MediumNumerical valueHas a figure
  4. 6 Apr 2023, Shift 1 · Q73Compound P (M.F. C14H13ON\mathrm{C_{14}H_{13}ON}; M.F. = MOLECULAR FORMULA) on treatment with HCl, Δ\Delta gives a Filter step: Residue Q and…HardDiagram basedHas a figure
  5. 27 Jul 2022, Shift 1 · Q80Match List I with List II. List I | List II A. Benzenesulphonyl chloride | I. Test for primary amines B. Hoffmann bromamide reaction | II.…MediumMatch the list
  6. 29 Jul 2022, Shift 2 · Q77The Hinsberg reagent isEasySingle correctHas a figure
  7. 26 Jun 2022, Shift 2 · Q77Which statement is NOT correct for p-toluenesulphonyl chloride?EasySingle correct
  8. 3 Aug 2021, Shift 1 · Q49Match List I with List II : List I : A. Hell-Volhard-Zelinsky reaction ; B. Hinsberg’s reagent ; C. Isocyanide test ; D. Hoffmann…EasyMatch the list

Question text from the official JEE Main paper published by NTA; answer from the final answer key. Chapter, topic and idea tags, difficulty and skill are Lumi’s. This question needs a figure we do not reproduce; it is described in words above. Lumi analyses 108 of the 174 JEE Main shifts held from 2017 to 2026.