Title 02. STRUCTURE OF ATOM - 2.pdf ✅

1 JEE Advanced 2024 Aromatic Compounds 1. Which of the following method (s) is/are not used to prepare p - bromo aniline as major product. (A) NH2 2 2 Br ⎯⎯⎯→ H O NH2 Br (B) NH2 ⎯⎯⎯⎯→ CH COCl 3 2 3 Br ⎯⎯⎯→ FeBr NaOH/H O2 ⎯⎯⎯⎯⎯→  NH2 Br (C) NH2 ⎯⎯⎯→ H SO 2 4 2 3 Br ⎯⎯⎯→ FeBr NH2 Br (D) NH2 NaNO /HCl 2 ⎯⎯⎯⎯⎯→ KCN CuCN  ⎯⎯⎯→ ⎯⎯⎯→ LiAlH4 2 3 Br ⎯⎯⎯→ FeBr NH2 Br 2. OH + X ( ) ( ) i NaOH ⎯⎯⎯⎯⎯⎯→ ii Acidification OH COOH + OH COOH X is/are (A) CHCl3 (B) CCl4 (C) CO2 (D) HCOOH 3. Which product is/are not obtained in following reaction: (i) CHCOCl/Anhy.AlCl 3 3 (ii) Ph3P = CH – CH3 (iii) BH3 /THF (iv) H2O2 /OH  (A) OH (B) OH (C) OH (D) OH 4. Which of the following statements is incorrect for electrophilic substitution. (A) Ortho - and para - directing groups increase electron density at ortho-and para-positions (B) Meta-directing groups increase electron density at meta-position (C) Meta-directing groups decrease electron density only at meta-position (D) Ortho-and para-directing groups decrease electron density at meta-position DPP-02
2 5. The reactivity of compound Z with different halogens under appropriate conditions is given below– OH Z C(CH)3 3 X2 Mono halo substituted derivative when X2 = I2 di halo substituted derivative when X = Br 2 2 tri halo substituted derivative when X = Cl 2 2 The observed pattern of electrophilic substitution can be explained by- (A) The steric effect of the halogen (B) The steric effect of the tert-butyl group (C) The electronic effect of the phenolic group (D) The electronic effect of the tert-butyl group 6. An aromatic chiral compound G C H Br ( 8 8 2 ) on treatment with NaOH / DMSO gives H C H BrO ( 8 9 ) . On heating 'G' with potassium tert-butoxide I C H Br ( 8 7 ) is formed. With one equivalent of methyl magnesium bromide in ether p-bromoisopropylbenzene is formed which observations is/are correct about these reactions. (A) (I) is an optically inactive aromatic alkene (B) H is an optically active alcohol (C) G = Br Br (D) Benzylic halide gives nucleophilic substitution with faster rate than aryl halide 7. O CH3 H SO 2 4 ⎯⎯⎯→ Product In the above reaction which of the following is observed (A) Dehydration (B) ArSE 2 (C) Acid-base reaction (D) Aromatisation 8. Number of possible monochlorinated isomer of R Cl C O COONa P in Anhy-AlCl3 Q Zn-Hg HCl R 9. Complete the following reaction with appropriate structures of products/reagents & find D.B.E. / DU of (B) ? CH=CH2 ( ) ( ) ( ) ( ) ( ) 2 3 3 Br i NaNH 3 equiv. ii CH I ⎯⎯→ ⎯⎯⎯⎯⎯⎯⎯→ A B
3 Comprehension-1 (Q.10 to 11) II H2SO4 SO3 H2SO4 HNO3 I Br A C B CO2H Mg D then H E F heat H + III major product IV minor product + CH2OH CHO HO Alkenes 10. Identify II product (A) NO2 (B) SO3H (C) CH3 (D) N = 0 11. (III) major product is? (A) (B) (C) (D) COOH Comprehension-2 (Q.12 to 13) For given reaction sequence molecular formula for compound ‘U’ is C7H6O2 & P gives negative Fehling test. P + Q NaOH  R O3 Zn,H2O S + P W T HgSO4 H2SO4 CrO Cl 2 2 Red V NaOH CaO, U Hot Fe tube KMnO4 12. Compound which is not a hydrocarbon (A) W (B) R (C) T (D) V 13. Compounds S is (A) CH3 – CH = O (B) Ph – CH = O (C) CH = O CH = O (D) CH – CH2 – CH O O
4 14. Match the column I and II Column-I Column-II (Group) (Effect on phenyl group) (A) N O (P) Activating group (B) (Q) De-activating group (C) O–CH–CH2 (R) o/p-director (D) S–Et (S) meta-director 15. Match the following Column-I Column-II (Properties) (Compound) (A) CO2 is evolved from NaHCO3 (P) O – H (B) Gives Libermann nitroso test (Q) O – H O2N NO2 NO2 (C) Gives yellow oily liquid with NaNO2 + HCl (R) H – N – Me (D) Evolve a colour less with active metals (S) N H