1 EMISTRY ING IRLE
1. The test is of 1 hour duration. 2. The maximum marks are 180. 3. This test consists of 45 questions. Test ate: 19.11.2017 (Level 1) Topic: xygen ontaining rganic ompound RE INSTRUTINS REFULLY 4. Keep your mobiles switched off during Test in the alls. (Single orrect hoice Type) Negative Marking [-1] This Section contains 45 multiple choice questions. Each question has four choices ), ), ) and ) out of which NLY NE is correct. Marks: 45 4 = 180 1. Which set of the following reagents would you select to convert 6 5 3 to the following alcohol 3 3 65 3 a. 3 ( 2 ) 2 Mgr and acid hydrolysis b. ( 3 ) 2, ll 3 r c. ( 3 ) 2 Mgr and acid hydrolysis d. ( 3 ) 2 (), Zn 2. Which of the following is incorrect reagent used to distinguish the pair of compound olumn I olumn II (Reagent). 3 2 N 2 & 3 N 3 a. N 2. 3 3 & 3 b. NP. 3 & 3 2 5 c. Na 3. 2 5 & 3 d. Iodoform Sol. oth will give NP Test 3. Which of the following alcohol on heating with u will give alkene a. ( 3 ) 3 b. ( 3 ) 2 c. 3 2 d. 3 2 3 Sol. 3 substrate forms alkene 4. The dehydration reaction 3 3 () 3 + (- 2) produces 2 EMISTRY ING IRLE
3 2 3 a. b. 3 3 2. 3 c. d. 5. ketoxime on eckmann rearrangement gives N-methyl propanamide. The configuration of ketoxime is Me a. N b. Et = 2 c. oth of these d. None of the above 6. n organic compound containing one oxygen gives red colour with ceric ammonium nitrate solution decolourise alkaline potassium permanganate solution, responds to iodoform test and shows geometrical isomerism. The compound is Et Me N a. b. c. d. Sol. ceric ammonium nitrate red colour (alcoholic group) KMn 4 decolorisation I 2/K Iodoform presence of 3 group 7. What are the products of the following reaction? 3 2, 2S 4 heat a. yclohexanol and ethanol b. 1, 2-cyclohexanediol and ethanal c. yclohexanol and ethanal d. 1, 2-cyclohexanediol and ethanol 3 EMISTRY ING IRLE
8. The compound which will not react with sodium is a. 2 5 b. 3 3 c. 3 3 d. 3 9. Which of the following does not give brick red precipitate with Fehling s solution a. cetaldehyde b. Formalin c. glucose d. cetone 10. hromic anhydride in 2 S 4 is turned blue by: a. 1 0 alcohol b. 2 0 alcohol c. d. all 11. From the following reactions. RNa + 2 R + Na R + NaN 2 RNa + N 3 Predict which of the following orders regarding base strength is correct: a. N 2 R b. c. R N2 12. Which will show tautomerism: d. N 2 R N2 R a. b. c. d. Sol. Rest have no - 13. Match the list: (i) Lil 4 2 () (ii) Lil 4 2 () 4 EMISTRY ING IRLE
(iii) Lil 4 2 () (iv) Lil 4 2 () a. (i), (ii), (iii), (iv) b. (i), (ii), (iii), (iv) c. (i), (ii), (iii), (iv) d. (i), (ii), (iii), (iv) 23 14. The IUP name of l 2 2 is: a. 5-chloro-3-penten-3-carbinol b. 1-chloro-3-penten-3-carbinol c. 4-chloro-2-ethyl-2-buten-1-ol d. 1-chloro-3-ethyl-2-buten-4-ol 15. End products of following sequence of reaction: r lc. K 3/ 2 a Sol. a. b. c. d. = ; = ( 2) 4 a 16. xidation of benzyl chloride with Pb(N 3 ) 2 gives a. benzoic acid b. benzene c. benzaldehyde d. none of these 17. The conversion 3 = 3 = 2 can be effected with a. Ni/ 2 b. 9 N c. Zn/g/l d. None of these Sol. l will react with double bond. 2 2 2 2 a + a 3 ll 3 Mgg/ TF 18. + 3 l. is l 3 3 3 3 a. b. c. d. 3 19. What is in the following reaction? 2 3 3 g 2 2 S 4 a. 3 b. 2 c. d. 5 EMISTRY ING IRLE
20. The product formed in the reaction is N 3 2 3 a. N b. 3 N 3 c. 3 N( 2 ) 3 d. 3 N( 2 ) 3 2 21. Phenol is least reactive for aromatic nucleophilic substitution because: a. arbon oxygen bond has some double bond character due to resonance b. xygen is present on sp 2 hybrid carbon which makes carbon oxygen bond stronger c. xygen is highly electronegative which decreases bond length between carbon and oxygen d. ll are correct 22. ( 3 ) 2 = 3 can be oxidised to ( 3 ) 2 = by a. hromic acid b. Nal c. u at 300 0 d. KMn 4 23. In the following reactions + + + K 1 ; + K 2 + + K 3 Which one is correct order? a. K 1 > K 2 > K 3 b. K 3 > K 2 > K 1 c. K 1 > K 3 > K 2 d. K 1 = K 2 = K 3 Sol. 1 st is romatic & III is antiaromatic 24. Which of the following undergoes decarboxylation most readily on being heated? a. b. c. d. Sol. -Keto cid 6 EMISTRY ING IRLE
25. No. of functional groups present in the following compounds is: 2N N a. 5 b. 7 c. 6 d. 8 26. Which of the following is a product (s) of following reaction? +? a. b. c. + 3 d. 27., Product of this annizaro reaction is : (50%) + + + 3 + 2 2 2 2 a. c. 28. () 3 714 Zn / c b. 2 2 2 2 d. ompound () exist in Geometrical isomers and () gives annizaro reaction: () will be: 3 a. 3 3 b. ( 3 ) 3 2 = 2 3 c. ( 3 ) 3 = 3 d. 3 2 2 Sol. ( 3 ) 3 3 ( 3 ) 3 3 29. 3 Mgr + () 3 + 3 Zn/ c r () Mg/ether () 3 + 3 3, is: a. b. c. d. 3 2 3 2 3 3 3 2 7 EMISTRY ING IRLE
30. Thiols are alcohol analogs in which the oxygen has been replaced by sulphur (e.g., 3 S). Given the fact that the S bond is less polar than the bond, which of the following statements comparing thiols and alcohols is correct? a. ydrogen bonding is weaker in thiols b. ydrogen bonding is stronger in thiols c. ydrogen bonding would be the same in both d. No comparison can be made without additional information 31. Ph = + 3 = () 87%; Product of this reaction is: base Et, a. Ph ( = ) 2 b. Ph ( = ) 3 c. Ph ( = ) 4 d. Ph = = 3 Sol. ldol condensation: 3 = Ph ( = ) 3 32. In the given reaction 65 2 S 4 3 65 3 6 5 3 65 3 the reaction intermediate is : a. 3 6 5 b. 3 65 3 65 3 65 c. 3 6 5 d. 3 65 65 3 2 = Ph = Ph = 2 = Θ 3 33. Which one of the following ketones does not react with 3 MgX: a. 3 3 b. 65 3 65 3 3 c. 3 d. 3 2 3 3 3 8 EMISTRY ING IRLE
34. The correct IUP name of the following compound is: 2N a. 7-nitro-4(carboxymethyl) heptanoic acid b. 6-nitro-3-(carboxy ethyl) hexanoic acid c. 4-(3-nitropropyl)hexane-1, 6-dioic acid d. 3-(3-nitro propyl) hexane-1, 6-dioic acid 35. onsider the following sequence of reactions. The final product () has the structure a. b. c. d. 3 Sl 2 ; + pyridine Sol. 36. In the reaction + l 3 1. Mg-g, benzene heat 2. 2, heat X the product (X) is a. b. c. d. 37. Rate of esterification is highest for the acid : a. 3 ( 2 ) 2 b. c. 3 d. l( 2 ) 4 38. In the given reaction : (i) r2 /P 3 [X], [x] will be (ii) NaN (iii) 2 / a. / 2 b. \ 2 2 2 c. d. 2 2 NaN 2 / Sol. 2 2 2 r N 9 EMISTRY ING IRLE
39. In the reaction sequence N 2 / 6 5 [x] P 2 5 / [Y] 2 22 [Z] [X], [Y] and {Z} respectively be a. 6 5 = N, 6 5 N, 6 5 b. 6 5 = N, 6 5 N 2, 6 5 c. 6 5 = N, 6 5, 6 5 N 2 d. 6 5 = N, 6 5 N, 6 5 N 2 40. n ester () with molecular formula 9 10 2 was treated with excess of 3 Mgr and the compound so formed was treated with conc. 2 S 4 to form olefin (). zonolysis of gave ketone with formula 8 8 which shows iodoform test positive. The structure of is: a. 6 5 2 5 b. 3 2 6 5 c. 3 6 5 3 d. 6 5 6 5 Sol. 2 5 3 Mgr 3 3Mgr 3 3 = + 3 3 / Zn = 2 3-2 Give iodoform 41. The refluxing of ( 3 ) 2 N 3 with 3 + gives : a. 2 3 N 2 + 3 b. 2 3 + 3 N 2 c. ( 3 ) 2 N + 3 d. ( 3 ) 2 N + 4 Sol. mide is hydrolysed to ( 3 ) 2 N & 3 42. Which compound will be formed when ethylacetate and excess of ethyl magnesium bromide allowed to react and product is hydrolysed? a. 3-Ethyl-3-pentanol b. 3-Methyl-3-pentanol c. hexan-3-ol d. 2-Methyl-2-propanol S 43. Silver acetate + I 2 2.... The main product formed in the reaction is: a. 3 I b. I 3 c. 3 I d. 3 3 Sol. 3 g I 2 3 I + gi + 2 3 g 3 3 + gi 10 EMISTRY ING IRLE
44. Which pair of reagent/name (or reaction) has been matched wrongly? Reagent Name a. Zn(g)/conc. l lemmensen b. N 2 4 /glycol, K Wolf Kischner c. Na/ N 3 () irch reduction d. us 4 + sodium potassium enedict Reagent tartarate Zn/ g 45. In the given reaction 65 65 [X] l X is : a. 65 2 65 b. 6 5 2 2 6 5 c. 6 5 l 2 6 5 d. 6 5 6 5 11 EMISTRY ING IRLE