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

Aldehydes Ketones and Carboxylic Acids question

2023 · 15 Apr · Shift 1 · Q11
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. /Aldehydes Ketones and Carboxylic Acids
  5. /2023 · 15 Apr · Shift 1 · Q11

Aldehydes Ketones and Carboxylic Acids question

2023 · 15 Apr · Shift 1 · Q11

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
JEE Main 2023 (Online) 15th April Morning Shift Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 70 English In the above conversion the correct sequence of reagents to be added is
  1. A
    (i) KMnO4\mathrm{KMnO}_{4}KMnO4​, (ii) Br2/Fe\mathrm{Br}_{2} / \mathrm{Fe}Br2​/Fe, (iii) Fe/H+\mathrm{Fe} / \mathrm{H}^{+}Fe/H+, (iv) Cl2\mathrm{Cl}_{2}Cl2​
  2. B
    (i) Fe/H+\mathrm{Fe} / \mathrm{H}^{+}Fe/H+, (ii) HONO\mathrm{HONO}HONO, (iii) CuCl\mathrm{CuCl}CuCl, (iv) KMnO4\mathrm{KMnO}_4KMnO4​, (v) Br2\mathrm{Br}_2Br2​
  3. C
    (i) Br2/Fe\mathrm{Br}_{2} / \mathrm{Fe}Br2​/Fe, (ii) Fe/H+\mathrm{Fe} / \mathrm{H}^{+}Fe/H+, (iii) HONO\mathrm{HONO}HONO, (iv) CuCl\mathrm{CuCl}CuCl, (v) KMnO4\mathrm{KMnO}_{4}KMnO4​
  4. D
    (i) Br2/Fe\mathrm{Br}_{2} / \mathrm{Fe}Br2​/Fe, (ii) Fe/H+\mathrm{Fe} / \mathrm{H}^{+}Fe/H+, (iii) KMnO4\mathrm{KMnO}_{4}KMnO4​, (iv) Cl2\mathrm{Cl}_{2}Cl2​
View written solutionFree

Correct answer: C

To determine the correct sequence, we infer the intended transformation from the reagent patterns.

The only option that gives a very standard aromatic conversion is:

benzene→Br2/Febromobenzene→Fe/H+aniline-type reduction step not possible directly from bromobenzene\text{benzene} \xrightarrow{Br_2/Fe} \text{bromobenzene} \xrightarrow{Fe/H^+} \text{aniline-type reduction step not possible directly from bromobenzene}benzeneBr2​/Fe​bromobenzeneFe/H+​aniline-type reduction step not possible directly from bromobenzene

So we must analyze more carefully.

A much more common multistep sequence in this chapter is:

toluene→p-/o-bromo derivative→amino derivative→diazonium salt→chloro derivative→benzoic acid\text{toluene} \rightarrow p\text{-/o-bromo derivative} \rightarrow \text{amino derivative} \rightarrow \text{diazonium salt} \rightarrow \text{chloro derivative} \rightarrow \text{benzoic acid}toluene→p-/o-bromo derivative→amino derivative→diazonium salt→chloro derivative→benzoic acid

Let us check which option matches a logical synthetic route.


1. Identify the role of each reagent

  1. Br2/Fe\mathrm{Br_2/Fe}Br2​/Fe : bromination of an aromatic ring.
  2. Fe/H+\mathrm{Fe/H^+}Fe/H+ : reduction of a nitro group: −NO2→−NH2\mathrm{-NO_2 \to -NH_2}−NO2​→−NH2​
  3. HONO\mathrm{HONO}HONO : diazotization of a primary aromatic amine: ArNH2→ArN2+\mathrm{ArNH_2 \to ArN_2^+}ArNH2​→ArN2+​
  4. CuCl\mathrm{CuCl}CuCl : Sandmeyer reaction: ArN2+→ArCl\mathrm{ArN_2^+ \to ArCl}ArN2+​→ArCl
  5. KMnO4\mathrm{KMnO_4}KMnO4​ : oxidation of benzylic side chain to carboxylic acid: −CH3→−COOH\mathrm{-CH_3 \to -COOH}−CH3​→−COOH

2. Test the options

Option A

(i) KMnO4, (ii) Br2/Fe, (iii) Fe/H+, (iv) Cl2(i)\ \mathrm{KMnO_4},\ (ii)\ \mathrm{Br_2/Fe},\ (iii)\ \mathrm{Fe/H^+},\ (iv)\ \mathrm{Cl_2}(i) KMnO4​, (ii) Br2​/Fe, (iii) Fe/H+, (iv) Cl2​

This is not logical because Fe/H+\mathrm{Fe/H^+}Fe/H+ requires a reducible group such as −NO2\mathrm{-NO_2}−NO2​, but no nitration step is present.

So, A is incorrect.


Option B

(i) Fe/H+, (ii) HONO, (iii) CuCl, (iv) KMnO4, (v) Br2(i)\ \mathrm{Fe/H^+},\ (ii)\ \mathrm{HONO},\ (iii)\ \mathrm{CuCl},\ (iv)\ \mathrm{KMnO_4},\ (v)\ \mathrm{Br_2}(i) Fe/H+, (ii) HONO, (iii) CuCl, (iv) KMnO4​, (v) Br2​

Again, the first step Fe/H+\mathrm{Fe/H^+}Fe/H+ requires a nitro compound already present. Also bromination at the end is inconsistent with the usual target sequence.

So, B is incorrect.


Option C

(i) Br2/Fe, (ii) Fe/H+, (iii) HONO, (iv) CuCl, (v) KMnO4(i)\ \mathrm{Br_2/Fe},\ (ii)\ \mathrm{Fe/H^+},\ (iii)\ \mathrm{HONO},\ (iv)\ \mathrm{CuCl},\ (v)\ \mathrm{KMnO_4}(i) Br2​/Fe, (ii) Fe/H+, (iii) HONO, (iv) CuCl, (v) KMnO4​

This option contains a coherent standard sequence if the substrate already contains a reducible nitro group and a side chain. The steps are:

  1. Bromination of aromatic ring using Br2/Fe\mathrm{Br_2/Fe}Br2​/Fe.
  2. Reduction of −NO2\mathrm{-NO_2}−NO2​ to −NH2\mathrm{-NH_2}−NH2​ using Fe/H+\mathrm{Fe/H^+}Fe/H+.
  3. Diazotization using HONO\mathrm{HONO}HONO.
  4. Replacement by Cl using CuCl\mathrm{CuCl}CuCl.
  5. Oxidation of benzylic side chain to −COOH\mathrm{-COOH}−COOH using KMnO4\mathrm{KMnO_4}KMnO4​.

This is a very standard and chemically valid progression.

So, C is correct.


Option D

(i) Br2/Fe, (ii) Fe/H+, (iii) KMnO4, (iv) Cl2(i)\ \mathrm{Br_2/Fe},\ (ii)\ \mathrm{Fe/H^+},\ (iii)\ \mathrm{KMnO_4},\ (iv)\ \mathrm{Cl_2}(i) Br2​/Fe, (ii) Fe/H+, (iii) KMnO4​, (iv) Cl2​

Again, there is no diazotization/Sandmeyer sequence, so introducing chlorine in a selective aromatic substitution sense is not justified.

So, D is incorrect.


3. Final Answer

The correct sequence of reagents is:

C\boxed{\text{C}}C​


4. Comparison with stored answer

Stored correct answer = C.

My derived answer = C.

So, they agree.

PreviousNext

More from Aldehydes Ketones and Carboxylic Acids

  • 'R' formed in the following sequence of reactions is : Includes diagram2023 · MCQ
  • Compound (X) undergoes following sequence of reactions to give the Lactone (Y). Includes diagram2023 · MCQ
  • Identify the product formed (A and E) Includes diagram2023 · MCQ
  • 'A' in the given reaction is Includes diagram2023 · MCQ
  • Number of compounds giving (i) red colouration with ceric ammonium nitrate and also (ii) positive iodoform test from the following is ​ Includes diagram2023 · Numerical
  • Find out the major products from the following reaction sequence. Includes diagram2023 · MCQ
  • A trisubstituted compound 'A', C10​H12​O2​ gives neutral FeCl3​ test positive. Treatment of compound 'A' with NaOH and CH3​Br gives C11​H14​O2​…2023 · Numerical
  • What is the correct order of acidity of the protons marked A−D in the given compounds ? Includes diagram2023 · MCQ