VIBRANT ACADEMY (India) Private Limited OCET- 3 OCET-3_(Alkyl Halide, Aryl Halide & Grignard Reagent) Single Choice Question : 1. 2. Which halide ion is the best nucleophile in dimethyl sufoxide solution ? (A) Fluoride (B) Chloride (C) Bromide (D) Iodide Which of the following reactions is not possible? (A) R – OH + NaBr ¾® R – Br + NaOH (B) R – OH + HBr ¾® R – Br + H2O (C) both reactions are possible (D) both reactions are not possible +– KSH NBS ¾¾ ¾® ( A ) ¾¾ ¾® (B) 3. Product (B) is (A) 4. (C) (D) What will be the final product ? (A) 5. (B) (B) (C) (D) Predict the major product of the following reaction. (A) (B) (C) (D) Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [1] 6. The product obtained from the reaction is : (A) (C) 7. (B) 2 (D) 2 Choose the product of the following reaction. 3 (A) 8. (B) (C) 3 (D) Predict the major product of the following reaction sequence. (A) 9. 3 3 (B) (C) (D) Choose the major product of the following reaction sequence. major product (A) (B) (C) (D) Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [2] 10. Predict the major product of the below reaction sequence : 2 (A) 11. (B) (C) (D) What will be the major product of the following reaction ? NaNH CH CH – I HÅ 3 2 2 ¾¾¾¾ ® (A) ¾¾¾¾¾ ® (B) ¾¾¾ ® (C) (1 mole) (excess) (A) 12. (B) (C) (D) Most reactive toward SN2 reaction. (A) 13. major (B) (C) Ph – CH2 – Cl (D) Ph – CH2 – CH2 – Cl Final product B is (B) (A) Ph – CH2 – O – SO2 – Ph (B) CH3 – CH2 – O – SO2 – Ph (C) (D) Ph – CH2 – O – CH3 Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [3] 3 14. 3 (A) and (B) will be respectively (A) (B) 3 3 (C) (D) Correct relation ship between (Q) and (S) is (A) Diastereomer (B) Enantiomer (C) Structural Isomer 15. 16. In the following case configuration about chiral C() is retained : 3 (A) (C) 17. (D) Identical (B) (D) in two case What product(s) would you expect to obtain from the following reaction? 3 (A) (B) (C) (D) Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [4] 18. Which of the following schemes will proceed to give the compound indicated as the major product. (1) (2) (3) (A) (1) only 19. (B) (1) and (2) (C) (1) and (3) (D) (2) and (3) Final product B is (B) (A) Ph – CH2 – O – SO2 – Ph (C) 20. (D) Ph – CH2 – O – CH3 Which is the correct major product of the following reaction? (A) 21. (B) CH3 – CH2 – O – SO2 – Ph (B) (C) (D) What is the major product of the following reaction ? (A) (C) (D) (D) Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [5] 22. What is the major product of the following reaction ? (A) 23. (B) (C) (D) The major products A and B for the following reactions are, respectively : (A) (B) (C) (D) 24. Compare rate of elimination bimolecular. Cl (A) a > b > c > d (B) a > c > b > d (C) b > a > c > d (D) b > d > a > c Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [6] 25. In given paris which compound is more reactive toward E2 reaction. (P) (Q) (R) (S) Ph - CH2 - CH2 - Br ( VII) (A) P – II, Q – III, R – V , S – VII (C) P – I < Q – III , R – VI , S – VII 26. Which of following compound is most reactive toward E2 reaction when they reacts with Zn/dust. (A) 27. 28. (B) P – II , Q – III, R – VI , S – VII (D) P – I , Q – II , R – V , S – VIII (B) (C) (D) Which of following is true for SNAr rate (A) SNAr rate of (B) SNAr rate of (C) SNAr rate of (D) SNAr rate of Which of the following is the major product from this reaction? 2 2 5 2 5 2 (A) (B) (C) (D) Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [7] 29. The major product of the following reaction is : 3 6 5 2 2 3 5 (B) (C) (D) P, P is : (A) 32. 5 2 (A) 30. 31. 2 (B) (C) (D) Free energy profile for given reaction is (A) (B) (C) (D) In the following sequence of reactions, [AIEEE-2007] Mg HCHO H2 O P + l2 ¾® B ¾¾ ¾ ¾® C ¾¾ ¾® D CH3CH2OH ¾¾ ¾® A ¾¾ ether the compound ‘D’ is : (A) butanal (B) n-butyl alcohol (C) n-propyl alcohol (D) propanal Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [8] 33. Which one of the following is the strongest base in aqueous solution? (A) Trimethylamine 34. (B) Aniline (C) 36. (D) Methylamine The treatment of CH3MgX with CH3C º C–H produces (A) CH3 – CH = CH2 35. (C) Dimethylamine [AIEEE-2007] [AIEEE-2008] (B) CH3C º C – CH3 3 (D) CH4 3 The gas evolved on heating CH3MgBr in methanol is [JEE Mains (online) 2016] (A) Methane (D) HBr (B) Ethane (C) Propene The major product B formed in the following reaction sequence is [JEE Main (online ) 2018] 2 37. (A) (B) (C) (D) In the reaction, [IIT 2003] CH3MgBr Ethyl ester ¾¾ ¾¾ ¾® P, the poduct P will be ( Excess ) 2 (A) (B) 5 (C) 2 5 5 2 5 3 7 The order of reactivity of phenyl magnesium bromide with the following compounds is 3 3 (A) (II) > (III) > (I) (C) (II) > (I) > (III) 5 (D) 2 38. 2 [IIT 2004] 3 (B) (I) > (III) > (II) (D) All react with the same rate Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [9] 39. Phenyl magnesium bromide reacting with t-Butyl alcohol gives (A) Ph – OH 40. (B) Ph – H (C) [JEE 2005] (D) The major product in the following reaction is [IIT Advance - 2014] 1. CH MgBr , dry ether , 0 º C ¾¾ ¾3¾ ¾ ¾ ¾ ¾ ¾¾® 2. aq. acid (A) (B) (C) (D) 41. Identify the product (B). (A) (B) (C) (D) 3 42. 43. The correct order of reactivity towards RMgX is : (I) (II) (III) (A) I > II > III (B) II > I > III (C) III > II > I (D) I > III > II (C) (D) What will be the major product ? (A) (B) 3 3 Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [10] 44. Choose the major product of the following reaction ? – (A) 45. (B) (C) (D) Which of the following combinations of a Grignard reagent and a ketone can’t be used to synthesized 2phenyl-2-butanol ? MgBr O (A) (B) + CH –CH C CH (C) 2 3 3 (D) 3 2 46. 2 3 State the order of increasing order of reactivity towards CH3MgBr of the following functional groups : 2 (A) (iv) < (iii) < (ii) (i) 47. (B) (iii) < (i) < (ii) < (iv) (C) (i) < (ii) < (iii) < (iv) (D) (i) < (ii) < (iv) < (iii) Choose the reaction scheme that could not be used to prepare the following alcohol. (A) (B) (C) (D) 48. The reaction between CO2 and a Grignard reagent will yield : (A) An alkyl magnesium halide (B) An alcohol (C) Magnesium carbonate (D) A carboxylic acid 49. The reaction of aldehydes and ketones with Grignard reagents followed by hydrolysis is an example of (A) Electrophilic addition (B) Nucleophilic addtion (C) Nucleophilic substitution (D) Electrophilic substitution 50. The reaction of Grignard reagents and alcohols results in (A) Nucleophilic substitution (B) Oxidation (C) Acid-base reaction (D) Reduction Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [11] 51. Choose the major product of the following reaction. (A) 52. 53. (B) (C) (D) Primary alcohols can be obtained from the reaction of the RMgX with(A) CO2 (B) HCHO (C) CH3CHO (D) H2O Which one of the following reactions would produce secondary alcoholO O || || 1.LiAlH 4 (B) C6H5CCH3 ¾¾ ¾¾® 1.CH3MgBr (A) C6H5 CCH3 ¾¾ ¾¾ ¾® + 2 .H + 2.H O || 1.LiAlH 4 (C) CH3CHO ¾¾ ¾+¾® 2.H 54. 55. 1.OH- (D) CH3CCH3 ¾¾ ¾ ¾® 2.Br2 When phenyl magnesium bromide reacts with t-butanol, the product would be : (A) Benzene (B) Phenol (C) t-butyl benzene (D) t-butyl ether Consider the structure of given alcohol OH | C 6 H 5 - C - CH 3 | C2 H5 This alcohol can be prepared from : O || C6 H 5 - C - CH 3 and C2H5MgBr (B) O || CH 3 - CH 2 - C - CH 3 and C6H5MgBr O || (C) C H - C - C H and CH3MgBr 6 5 2 5 (D) All of these (A) 56. Predict the product of the following reaction. 2 2 (A) (B) (C) (D) Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [12] 57. Predict the product of the following reaction sequence. (A) 58. (B) (C) (D) Choose the best reagents to carry out the following reaction : (A) D2, Pt (B) 1. Mg, Ether, D2O (C) D2SO4, D2O, D (D) D3O+ , Acetone, D 59. Acetyl bromide reacts with excess of CH3MgI followed by treatment with a saturated solution of NH4Cl given (A) acetone (B) acetyl iodide (C) 2- methyl -2- propanol (D) acetamide 60. Phenyl magnesium bromide reacts with methanol to give (A) a mixture of anisole and Mg(OH)Br (B) a mixture of benzene and Mg(OMe)Br (C) a mixture of toluene and Mg(OH)Br (D) a mixture of phenol and Mg(Me)Br 61. The treatment of CH3MgX with CH3C º C–H produces (A) CH3 – CH = CH2 (B) CH3C º C – CH3 (C) 62. 64. (D) CH4 3 The order of reactivity of phenyl magnesium bromide with the following compounds is 3 63. 3 3 3 (A) (II) > (III) > (I) (C) (II) > (I) > (III) (B) (I) > (III) > (II) (D) All react with the same rate (CH3)3CMgCl on reaction with D2O produces (A) (CH3)3CD (C) (CD)3CD (B) (CH3)3COD (D) (CD)3COD What is the major product of the following reaction ? 2 (A) (B) (C) (D) Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [13] MCQ : 65. In the following case configuration about chiral C( ) is retained : 3 (A) (B) (C) 66. (D) Which is correct reactivity order for the following reaction. (A) CH3–CH2–Br > > For SN2 (B) For SN1 (C) > (D) CH3–CH2–Br > 67. > > > for E1 For E2 In which of following reaction Diastereomer isomer will formed. KOH (A) ¾¾ ¾® (C) 2® ¾¾ ¾¾ D NaNH D (B) (D) t -BuO QK Å ¾¾ ¾ ¾ ¾ ¾® D alc . KOH ¾¾ ¾ ¾ ¾® D Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [14] Matching List 68. List-I List-II (P) (1) SN1 (Q) (2) SN2 (R) (3) Carbocation is intermediate (S) (4) Carbanion is intermediate Codes : (A) (B) (C) (D) 69. P 1 1 2 2 Q 2 2 1 1 R 4 3 4 3 S 3 4 3 4 List-I List-II (P) (1) SN1 (Q) (2) SN2 (R) (3) SNi (S) (4) SN NGP 14 2 2 Codes : (A) (B) (C) (D) P 3 1 2 1 Q 2 3 1 2 R 1 2 4 3 S 4 4 3 4 Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [15] Integer 70. How many stereo isomeric optically active compounds of molecular formula C4H8O which contains no double bond and evolve a gas when treated with CH3MgI ? 71. 2 How many equivalent ‘x’ are used in the above reaction ? 72. Total number of products obtained when this substrate is subjected to E2 reaction will be (including streoisomer). 73. 74. 75. Calculate total number of alkene products when 2-chloro-2-cyclobutyl hexane react with alcoholic KOH and heat. In the following figure, x and y represent the number of times of HEME takes place to remove nitrogen from the compound. (HEME = Hofmann Exhaustive Methylation followed by Elimination) EtOH ¾¾ ¾ ¾® (x) Total number of SN products. s. 1 D aq. KOH ¾¾ ¾¾® (y) Number of nucleophilic substitution bimolecular (SN2) products. Sum of (x + y) will be 76. How many 1,2-shifts are involved during following conversion- Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [16] 77. In the given reactions (a), (b) and (c) total number of (SN1 + E1) products are X, Y and Z respectively. (a) (X), (b) (c) find the value of (X + Y – Z = ?) 78. 2 2 4 4 Sum of a-hydrogen in alkene (A + B) is 79. Find out number of alcohol that can give positive iodoform test , , , , , , , Vibrant Academy (I) Pvt. Ltd. "B-41" Road No.2, IPIA, Kota (Raj.) Ph. 06377791915 (www.vibrantacademy.com) [17]