Consider the following sequence of reactions.
The image illustrates the multi-step conversion of 4-nitrotoluene into a brominated acetanilide derivative.
Assuming that the reaction proceeds to completion, then 137 mg of 4-nitrotoluene will produce ____mg of B.
(Given molar mass in g mol⁻¹$^{-1}$ H : 1, C : 12, N : 14, O : 16, Br : 80)
A.301$\text{301}$
B.146$\text{146}$
C.228$\text{228}$
D.208$\text{208}$
Solution & Explanation
Core Logic
Follow the sequence of chemical transformations to determine the structure of product B, then apply stoichiometry based on moles of the starting material to find its final mass.
Step 1: Reaction Sequence Analysis
Reaction 1: Reduction of 4-nitrotoluene using Sn, HCl / Δ$Sn, HCl / \Delta$ followed by pH neutralization converts the -NO₂$-NO_2$ group to an -NH₂$-NH_2$ group, forming 4-methylaniline (p-toluidine).
The image illustrates the multi-step conversion of 4-nitrotoluene into a brominated acetanilide derivative.
Step 2: Acetylation
Reaction 2 (forming A): The aniline group is protected by reaction with acetic anhydride (CH₃CO)₂O$(CH_3CO)_2O$, forming an acetanilide derivative (N-(4-methylphenyl)acetamide).
The image illustrates the multi-step conversion of 4-nitrotoluene into a brominated acetanilide derivative.
Step 3: Bromination
Reaction 3 (forming B): Bromination using Br₂ / AcOH$Br_2 / AcOH$. The -NHCOCH₃$-NHCOCH_3$ group is strongly activating and ortho-directing, while the -CH₃$-CH_3$ group is weakly activating and ortho-directing. The incoming -Br$-Br$ will substitute ortho to the -NHCOCH₃$-NHCOCH_3$ group due to dominant directing influence.
The image illustrates the multi-step conversion of 4-nitrotoluene into a brominated acetanilide derivative.
Step 4: Stoichiometric Calculation
Molar mass of 4-nitrotoluene (C₇H₇NO₂$C_7H_7NO_2$) = 137 g/mol$137 \text{ g/mol}$.
Molar mass of product B (C₉H₁₀BrNO$C_9H_{10}BrNO$) = 228 g/mol$228 \text{ g/mol}$.
Since the stoichiometry is 1:1 and yields are 100%, moles of B = 0.001 mol$0.001 \text{ mol}$.
Mass of B = 0.001 mol × 228 g/mol = 0.228 g = 228 mg$0.001 \text{ mol} \times 228 \text{ g/mol} = 0.228 \text{ g} = 228 \text{ mg}$.
Pattern Recognition
When dealing with multi-step synthesis yield questions, immediately check the initial and final molar masses if the reaction achieves 100% completion. Often, 1 mole of reactant gives 1 mole of product.
Keywords:#reaction proceeds to completion#JEE Main 2026 Morning Q57#Amines JEE Main 2026#Reactions of Aromatic Amines JEE Main 2026#reaction sequence#4-nitrotoluene#chemical synthesis
More Amines Previous-Year Questions — Page 5
Qjee_main_2025_08_april_eveningFunctional Group Analysis and Identification
An organic compound 'A' undergoes the following sequence of transformations:
'A' [(ii) H₃O^+](i) NaOH 'B' [(ii) H₂SO₄, Δ](i) EtOH 'C'$$\text{'A'} \xrightarrow[\text{(ii) } H_3O^+]{\text{(i) } NaOH} \text{'B'} \xrightarrow[\text{(ii) } H_2SO_4, \Delta]{\text{(i) } EtOH} \text{'C'}$$
* 'A' shows a positive Lassaigne's test for nitrogen and its molar mass is 121 g mol⁻¹$121 \text{ g mol}^{-1}$.
* 'B' gives effervescence with aqueous NaHCO₃$\text{NaHCO}_3$.
* 'C' gives a characteristic fruity smell.
Identify A, B, and C from the options below:
A.
B.
C.
D.
Solution
Core Logic
Let's perform a step-by-step diagnostic analysis:
Molar Mass & Nitrogen Test: Compound 'A' has a nitrogen atom and a molar mass of 121 g mol⁻¹$121 \text{ g mol}^{-1}$. Let's verify Benzamide (C₆H₅CONH₂$\text{C}_6\text{H}_5\text{CONH}_2$):
Benzoic acid reactively gives effervescence with NaHCO₃$\text{NaHCO}_3$ due to the liberation of CO₂$\text{CO}_2$ gas.
Esterification: Reaction of benzoic acid with ethanol in the presence of acid catalyst results in the creation of ethyl benzoate, an ester with a pleasant fruity smell:
"Fruity smell" is an absolute indicator for an ester product. "Effervescence with NaHCO₃$\text{NaHCO}_3$" dictates a carboxylic acid intermediate. Basic hydrolysis converting an organo-nitrogen compound into an acid points directly to an amide or a nitrile—molar mass calculation establishes benzamide over benzonitrile (M = 103$M = 103$).
Chapter Mix
Class 12 Chemistry: Amines
Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids
Q41jee_main_2025_29_jan_eveningDiazotization and Coupling Reactions
Which one of the following reaction sequences will give an azo dye?
(1) Nitrobenzene treated with (i) Sn/HCl$Sn/HCl$, (ii) NaNO₂/HCl$NaNO_{2}/HCl$, (iii) β$\beta$-naphthol, NaOH$NaOH$
(2) Benzenesulfonic acid treated with (i) SOCl₂$SOCl_2$, (ii) NH₃$NH_3$, (iii) Benzyl chloride
(3) Benzonitrile treated with (i) 70% H₂SO₄$70\% H_2SO_4$, (ii) PCl₅$PCl_5$, (iii) Aniline
(4) Aniline treated with (i) HCl/NaNO₂$HCl/NaNO_2$, (ii) Toluene
A. Reaction sequence (1)
B. Reaction sequence (2)
C. Reaction sequence (3)
D. Reaction sequence (4)
Solution
Core Logic
Let's track sequence (1):
Nitrobenzene (Ph-NO₂$Ph-NO_2$) is reduced using Sn/HCl$Sn/HCl$ to form Aniline (Ph-NH₂$Ph-NH_2$).
Aniline undergoing diazotization with NaNO₂/HCl$NaNO_{2}/HCl$ at cold temperatures (0-5circC$0-5^{circ}C$) creates Benzene diazonium chloride (Ph-N₂⁺Cl⁻$Ph-N_{2}^{+}Cl^{-}$).
The diazonium salt undergoes a coupling reaction with β$\beta$-naphthol in alkaline conditions (NaOH$NaOH$) to synthesize a highly vibrant red-orange azo dye.
Diazotization and Coupling Reactions diagram for Q41 - JEE Main 2025 Evening
Pattern Recognition
The standard sequence for azo dye preparation is: Aromatic Nitro arrow$\rightarrow$ Primary Amine arrow$\rightarrow$ Diazonium Salt arrow$\rightarrow$ Phenol/Naphthol Coupling.
Chapter Mix
Class 12 Chemistry: Amines
Q49jee_main_2025_28_jan_morningYield and Stoichiometric Calculations
Consider the following sequence of reactions :
The flowchart tracks a chemical conversion starting from chlorobenzene down to final compound B.
11.25 mg of chlorobenzene will produce x × 10⁻¹$\mathrm{x} \times 10^{-1}$ mg of product B.
(Consider the reactions result in complete conversion.)
[Given molar mass of C, H, O, N and Cl as 12, 1, 16, 14 and 35.5g mol⁻¹$35.5\mathrm{g\,mol}^{-1}$ respectively]
Numerical Answer.Answer: 93 to 93
Solution
Core Logic
The reaction sequence details the functional conversion of chlorobenzene down to product B (aniline, with a molar mass of 93 g mol⁻¹$93\,\mathrm{g\,mol}^{-1}$).
Following stoichiometric preservation:
moles of chlorobenzene = moles of Aniline (B)$$\text{moles of chlorobenzene} = \text{moles of Aniline (B)}$$
Molar mass of chlorobenzene (C₆H₅Cl$\mathrm{C}_6\mathrm{H}_5\mathrm{Cl}$) = 112.5 g mol⁻¹$112.5\,\mathrm{g\,mol}^{-1}$.
The flowchart tracks a chemical conversion starting from chlorobenzene down to final compound B.
Mass = 10⁻⁴ mol × 93 g mol⁻¹ = 9.3 × 10⁻³ g = 9.3 mg$$\text{Mass} = 10^{-4}\,\mathrm{mol} \times 93\,\mathrm{g\,mol}^{-1} = 9.3 \times 10^{-3}\,\mathrm{g} = 9.3\,\mathrm{mg}$$
Expressing in the specified format:
9.3 mg = 93 × 10⁻¹ mg ⇒ x = 93$$9.3\,\mathrm{mg} = 93 \times 10^{-1}\,\mathrm{mg} \Rightarrow x = 93$$
Pattern Recognition
Sees: Conversion sequence preserving a 1:1 mole ratio layout.
Shortcut: Directly compute target weight via WB = WA · (MB)/(MA) = 11.25 · (93)/(112.5) = 9.3$W_B = W_A \cdot \frac{M_B}{M_A} = 11.25 \cdot \frac{93}{112.5} = 9.3$.
Chapter Mix
Class 12 Chemistry: Amines
Q37jee_main_2025_03_april_morningDiazonium Salts and Reactions
Identify [A], [B], and [C], respectively in the following reaction sequence: Reaction sequence starting from aniline reacting with NaNO2/HCl to give [A], which reacts with KI to give [B], and with 2Na/Dry ether to give [C].
Aniline with NaNO₂/HCl$\mathrm{NaNO_2/HCl}$ at 273--278~K$273\text{--}278\mathrm{~K}$ undergoes diazotization to yield benzenediazonium chloride [A] = C₆H₅N₂^+Cl^-$[\mathrm{A}] = \mathrm{C_6H_5N_2^+Cl^-}$.
Reaction of [A]$[\mathrm{A}]$ with KI$\mathrm{KI}$ replaces the diazonium group with iodine to form iodobenzene [B] = C₆H₅I$[\mathrm{B}] = \mathrm{C_6H_5I}$.
Treating iodobenzene [B]$[\mathrm{B}]$ with 2Na/dry ether$\mathrm{2Na/dry\ ether}$ yields biphenyl [C] = C₆H₅-C₆H₅$[\mathrm{C}] = \mathrm{C_6H_5-C_6H_5}$ via the Fittig reaction.
Reaction of benzenediazonium chloride with ethanol (EtOH$\mathrm{EtOH}$) is a reduction/deamination reaction that converts the diazonium salt to benzene, while ethanol gets oxidized to ethanal (CH₃CHO$\mathrm{CH_3CHO}$).
It does NOT yield phenetole (ethoxybenzene, Ar-OEt$\mathrm{Ar-OEt}$). Therefore, Reaction (1) is incorrect.
Step 1: Verification of Other Reactions
Reaction with H₃PO₂/H₂O$\mathrm{H_3PO_2/H_2O}$ gives benzene. (Correct)
Reaction with KI$\mathrm{KI}$ gives iodobenzene. (Correct)
Reaction with CuCN/KCN$\mathrm{CuCN/KCN}$ gives benzonitrile. (Correct)
Pattern Recognition
Diazonium salt + Ethanol arrow$\rightarrow$ Benzene (reduction), NOT Ethoxybenzene.
Chapter Mix
Class 12 Chemistry: Amines
More Amines Questions — jee_main_2026_23_january_morning
Practice past-year questions one chapter at a time. Pick an exam → subject → chapter and get every PYQ for that topic — pulled together from all past papers — with the chapter's key formulas alongside.