UGC POINT ACADEMY LEADING INSTITUE FOR CSIR-JRF/NET, GATE & JAM CHEMICAL SCIENCE TEST SEREIS # 2. Organic Chemistry. Instructions
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1 UGC PINT ACADEMY LEADING INSTITUE FR CSIR-JRF/NET, GATE & JAM BKLET CDE C Date: 24/11/2015 CEMICAL SCIENCE TEST SEREIS # 2 rganic Chemistry SUBJECT CDE 01 Timing: 2:00 Maximum Marks: 80 Instructions 1. This test paper has a total of 35 questions carrying 70 marks. The entire question paper is divided in two sections, A and B. All sections are compulsory. Question in each section are different type. 2. Read the Questions carefully and mark your appropriate response to the MR sheet 3. There is Negative marking of 1/4 for Each wrong answer 4. Mark the response by Black or Blue Ball Pen only 5. Any other belongings like Book/ Notes / Electronic device etc are not permitted in the examination hall. 6. Submit your answer sheet (MR Sheet) to the invigilator before leaving the examination hall 7. Do not write in the question paper 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
2 1. The major product [A] is:- 2. The major product [A] & [B] is 3. The major product [A] is 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
3 4. The major product [A] is 5. The major product [A] & [B] is 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
4 6. The major product [A] is 7. The major product [A] is 8. The major product [A] is 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
5 9. Given the major product [A] & [B] is 10. Given the product [A] & [B] in the following reaction sequence: 11. Give the major product [A] in the following reaction 12. Give the major product [A] is 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
6 13. Give the major product [A] is 14. Give the major product [A] is 15. Give the major product [A] is 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
7 16. Give the major product [A] is 17. In the following reaction sequence, the reagent X and Y are respectively (1) X : PhS2, BF3 Et & Y : C2 CCEt, BF3 Et2 (2) X : PhS, PTSA 2 m CPBA & Y : C2 CCEt, BF3Et 2 (3) X : PhS3, BF3 Et & Y : LDA, C2 CCEt (4) X : PhS, PTSA, 2. m CPBA & Y : LDA, C2 CCEt 18. The major product [A] is 19. The major product [A] is 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
8 20. The major product [A] is 21. Give the suitable products C 3 Base (Et) [P] 3 C Et (1) (2) (3) C C 3 3 C Et C3 (4) 3 C C 3 Et 22. The major product of the following reaction sequence Br Br Br Br Br C C C (1) (2) (3) (4) C 23. rder the increasing C3Cl, C3Br, C3I max value of the following compounds (1) C3Cl C3Br C3I (2) C3Br C3I C3Cl (3) C3Br C3Cl C3I (4) C3Cl C3Br C3I 24. rder of C stretching frequency of the following compound (1) II > III > I (2) III > II > I (3) II > I > III (4) I > III > II 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
9 25. The correct sequence of -values of the 1 -NMR of hydrogen a, b, c, & d in the following compound (d) (b) C C 3 C C (a) (c) (1) 4.88, 4.57, 7.27, 2.2 (2) 4.57, 4.88, 7.27, 2.2 (3) 7.27, 4.57, 4.88, 2.2 (4) 7.27, 4.88, 2.2, The major product (A) 27. The major product (A) C + (A) 3 C C 3 (1) (2) (3) (4) 28. The number of isoprene unit in humulene molecules (1) 4 (2) 2 (3) 5 (4) Stereo chemical relation between structure I and II C 3 C 3 & C 3 C 3 (I) (II) (1) Enantiomer (2) Diastereomer (3) omomer (4) Chiral 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
10 30. In the following compound the 1 and 2 are the prochiral faces of (1) omotopic (2) Enantiotopic (3) Diastereotopic (4) None 31. Number of 13 C-NMR peaks in the following compounds respectively N (I) (II) (III) (1) 4, 2, 2 (2) 5, 2, 3 (3) 4, 2, 3 (4) 6, 2, Which of the following compound are aromatic N N N N (A) (B) (C) (D) (1) A & B (2) B and D (3) A & C (4) A, C & D 33. The p Ka value of C group is 4.8 and p Ka value of group is 10. What species would present if you dissolve the following compound in (a) water at p =7 and (b) in alkali solution at p =12; respectively 34. Identify the following compound A and B by given spectral data Cl NaN 2 1. RC t (A) 3 (B) Bu 2. LiI A C ; ppm : , s and , s Data: For 4 6 For B C ppm J z and quinetet J z 4 6 ; :3.02 4,triplet, 5 2,, 5 (1) A = ; B = (2) A = ; B = (3) A = ; B = C 3 C2 C 3 (4) A = ; B = C 3 3 C 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
11 35. Consider the following reaction R Ph Br Na Ph Product (A) is formed by (1) 2,3-Sigmatropic rearrangement (2) 3,3-sigmatropic rearrangement (3) 6 e ring closing conrotation (4) 1,5-sigmatropic reaction 36. The major product [B] is R 1. BuLi 2. + Ph (A) R 37. The major product [B] is 38. Which one is the correct intensity ratio for compound ClC2CBr2 in its mass spectrum (1) 27:27:9:1 (2) 3:7:5:1 (3) 1:3:3:1 (4) 9:15:7:1 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
12 39. The major product [A] is 40. The major product [A] is 41. Match the amino acid with their structures: (1) I-P, II-T, III-R (2) I-R, II-S, III-Q (3) I-P, II-Q, III-S (4) I-R, II-P, III-Q 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
13 42. The correct sequence of the amino acid present in the tripeptide given below is (1) Val-Ser-Thr (2) Val-Thr-Ser (3) Lu-Ser-Thr (4) Leu-Thr-Ser 43. The product formed in the reaction is 44. The following photochemical conversion proceeds through (1) Barton reaction (2) Paterno-Buchi reaction (3) Norrish-type-I reaction (4) Norrish type-ii-reaction 45. The major product [P] formed in the reaction is 46. The major product [P] formed in the reaction is 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
14 47. The major product [P] formed in the reaction is: 48. Provide the structure of the major organic product in the following reaction 49. Product [P] and [Q] respectively are as follows in the given reaction sequence: 50. The reaction between X & Y to give Z, proceeds via (1) 4 -conrotatory opening of X followed by endo Diels-Alder cycloaddition (2) 4 -disrotatory opening of X followed by endo Diels-Alder cycloaddition (3) 4 -conrotatory opening of X followed by exo Diels-Alder cycloaddition (4) 4 -disrotatory opening of X followed by exo Diels-Alder cycloaddition 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
15 51. The major product [P] in the following reaction 52. The major product of the following reaction 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
16 53. The major product [P] in the following reaction 54. Major product obtained in the following reaction 55. The major product obtained in the following reaction: 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
17 ANSWER KEY 1.(2) 2.(3) 3.(4) 4.(2) 5.(1) 6.(3) 7.(4) 8.(1) 9.(1) 10.(2) 11.(3) 12.(3) 13.(1) 14.(2) 15.(1) 16.(3) 17.(4) 18.(3) 19.(1) 20.(3) 21.(2) 22.(3) 23.(4) 24.(1) 25.(2) 26.(1) 27.(3) 28.(4) 29.(3) 30.(2) 31.(1) 32.(3) 33.(2) 34.(2) 35.(1) 36.(4) 37.(2) 38.(2) 39.(2) 40.(2) 41.(4) 42.(1) 43.(1) 44.(4) 45.(3) 46.(1) 47.(2) 48.(2) 49.(2) 50.(1) 51.(2) 52.(4) 53.(1) 54.(1) 55.(3) 27-G 2 ND FLR, JIA SARAI, NEAR IIT, NEW DELI
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