3 free radical is most stable. Q.5. A + Cl 2 hv monochloro product To maximize the yield of monochloro product in the above reaction? Cl 2 must be add

Transcription

1 Q.1. I II III IV IV III II I I III II IV IV II III I I II III IV The decreasing order of the anti knocking value of octane number of the following is: (I) CH 4 (II) C 2 H 6 (III) C 3 H 8 (IV) C 4 H 10 As the number of C atoms increases, Knocking power increases or anti knocking power decreases. Q.2. On catalytic reduction (H 2 /Pt) how many alkenes will give 2 methylbutane? Q.3. Which of the following compounds can be best prepared by Wurtz reaction? Iso butane n butane n pentane Iso pentane CH CH x+no+x CH CH C H n butane Q.4. Select the structure of the major product formed in the reaction

2 3 free radical is most stable. Q.5. A + Cl 2 hv monochloro product To maximize the yield of monochloro product in the above reaction? Cl 2 must be added in excess Reactant (A) must be added in excess Reaction must be carried out in dark Reaction must be carried out with equimolar mixture of Cl 2 and A Conceptual Q.6. Select the chain propagation steps in the free radical chlorination of methane. (1) Cl2 2Cl (2) Cl +CH4 CH3 Cl+H (3) Cl + CH4 CH 3+ HCl (4) H +Cl2 HCl + Cl (5) CH 3+ Cl2 CH3 Cl + Cl 2, 3, 5 1, 3, 6 3, 5 2, 3, 4 Chain initiation : Cl hv 2 2Cl Chain propagation : CH 4+ Cl CH 3+ HCl CH 3+ Cl2 CH3 Cl + Cl

3 Chain termination : H +H H 2 Cl + Cl H +Cl Cl 2 HCl Q.7. Br will abstract which of the hydrogen most readily. a b c d 3 Free redical. Q.8. Above reaction is an example of: Isomerization Polymerization Cracking De hydrogenation Isomerization Q.9. Which of the following is the major product when 1 buthanol is heated with concentrated H 2 SO 4? 1 butene Cis 2 butene Trans 2 butene All of the above Q.10. None of these

4 Q.11. Comment on optical activity of the products: Racemic Diastereomer Meso Optically pure enantiomer Due to the for motion of carbocation attack can take place from both the sides. Q.12. Identify (Z) in the above sequence of reactions: Q.13. Which compound would be the major product when (CH 3 ) 2 CHCHBrCH 2 Br is treated with alcoholic KOH? (CH 3 ) 2 CHCH 2 CHOHCH 3 (CH 3 ) 2 COCH 2 CH 2 CH 3 Correct Answer 4

5 Q.14. On catalytic reduction with H 2 /Pt how many alkenes will give n butane? Q.15. regent used for the reaction: LiAlH 4 H 2 /Ni NaBH 4 H 2, Pd BaSO 4 H 2,Ni Q.16. Give the major product of the following reaction 3, 3 dimethyl 1 butene + HCI Major 2 chloro 3, 3 dimethyl butane 2 chloro 2, 3 dimethyl butane 1,2 dichloro 3, 3 dimethyl butane 1 chloro 3, 3 dimethyl butane Q.17. the intermediate of reaction is:

6 Q.18. Q.19. Consider the addition of HBr to 3, 3 Dimethyl 1 butene shown below. What is the best mechanistic explanation for the formation of the observed product? Protonation of the alkene followed by a hydride shift and addition of bromide to the carbocation Double bond shift in the alkene following by the protonation and addition of bromide to the carbocation Addition of bromide the alkene followed by a double bond shift and protonation Protonation of the alkene followed by a methyl shift and addition of bromide to the carbocation Correct Answer 4 Protonation of the alkene followed by a methyl shift and addition of bromide to the carbocation

7 Q.20. Arrange the above in the decreasing order of reactivity towards HBr: a b c b a c b c a a c b This O supports the carbocation making it stable. Q.21.

8 Q.22. Choose the correct major product for the reaction below: Correct Answer 4 Q.23. Both of these H + Alkene + H2O Alcohol Which of the following statements about this reaction is correct? It is Markovnikov addition of water to alkene. It involves carbonium ion rearrangement, if possible. Both of these None of these Q.24. In case of addition of HX to an alkene, Markovnikov originally stated that The H atom adds to the carbon atom of the double bond that already has greater number of H atoms and halide ion adds to the carbon atom of the double bond that has fewer number of ah atoms. The H atom adds to the carbon atom of the double bond that has fewer number of H atoms and halide ion adds to the carbon atom of the double bond that has greater number of H atom. Both of these depending upon situation None of these The H atom adds to the carbon atom of the double bond that already has greater number of H atoms and halide ion adds to the carbon atom of the double bond that has fewer number of ah atoms.

9 Q.25. None of these Example of oxidative cleavage Q.26. Identify the product of the reaction when molecule undergoes ozonolysis I is only product I and III I and Iv II and IV

10 Q.27. Which compound will yield 5 keto 2 methyl hexanal upon treatment with O 3? Q.28. Find the structure of (X).

11 Q.29. Ozonolysis of the following compound will produce; Q.30. Compound (A) is :

12 Q.31. An organic C 4 H 6 on ozonolysis give HCHO, CO 2, CH 3 CHO. Compound will be : CH 3 CHO CO 2 HCHO Q.32. Which of the following compound does not evolve CO 2 gas, when undergo oxidative ozonolysis? Correct Answer 4 Q.33. Product (C) is

13 Q.34. Identify the major product

14 Q.35. P should be Q.36. Rank the following compounds with respect to increasing acidity (1) 1 butene (2) Butane (3) 1 butyne (4) NH Greater the 5 chorocter more is acidity and NH 3 is more acidic and alkenes and alkanes Q.37. Which of the following reacts with Tollen s reagent giving white precipitate? 2 pentene 2 pentyne 1 butyne 1 butanol Alkynes on reaction with Tollen s reagent gives Triple bonds should be of extremer positions.

15 Q.38. Which of the following reagents can be distinguish propyne from propene? Br 2, CCl 4 Dilute KMnO 4 Conc. H 2 SO 4 AgNO 3 in NH 4 OH Correct Answer 4 AgNO 3 in NH 4 OH Q.39. Which is the most suitable reagent among the following distinguish compound (3) from the others? Bromine in carbon tetrachloride Bromine in acetic acid solution Alk. KMnO 4 Ammonical silver nitrate Correct Answer 4 Ammonical silver nitrate Q.40. Choose the reagent to carry out the reaction. H 2 + Lindlar catalyst Li + NH 3 Cons. H 2 SO 4 H 2 O + H + H 2 + Lindlar catalyst Q.41. Which of the following reacts with Tollen s reagent giving white precipitate? 2 pentene 2 pentyne 1 butyne 1 butanol 1 butyne Q.42. Which alkyne given 3 ethylhexane on catalytic hydrogenation?

16 All of these Correct Answer 4 All of these Q.43. Predict the product of the reaction 1 butyne with 2 equivalents of HCI Q.44. H CaC 2O RedhotCu tube A B 2 Calcium carbide Product (B) of the reaction is: Toluene Ethyl benzene Benzene Butyne CaC H O 2 Ca OH + HC CH 2 2 A, Q.45. How many benzylic hydrogens are present in the hydrocarbon shown?

17 Q.46. The middle oil fraction of coal tar distillation contains Benzene Naphthalene Anthracene Xylene Naphthalene Q.47. On heating a mixture of sodium benzoate and sodalime, the following is obtained Toluene Phenol Benzene Benzoic acid Q.48. Catalytic dehydrogenation of n heptane in the presence of Cr 2 O 3 /Al 2 O 3 at 750 K gives Iso heptane 1 heptane Toluene 2, 3 dimethyl pentene 1 Q.49. When sodium benzoate is heated with soda lime, the product formed is: Phenol Chlorobenzene Benzene Benzaldehyde Benzene Q.50. Among the following compounds that can be most readily nitrated is: benzene Benzaldehyde Toluene Chlorobenzene (because of +I support by CH 3 group)

18 Q.51 The electrophile in the reaction is + SO H 3 SO 2 SO 3 H 2 SO 4 SO 3 H Q.52 Nitrobenzene can be prepared from benzene by using a mixture of conc. HNO 3 and conc. H 2 SO 4. In the nitrating mixture, HNO 3 acts as a/an Base Acid Reducing agent Catalyst NO 2 is formed which acts as electrophile. Q.53 Which of the following compounds will not undergo Friedel Craft acylation when treated with CH 3 CH 2 COCl, AlCl 3? Toluene p Xylene Chlorobenzene Benzophenone Correct Answer 4 The groups which are highly on moderately deactivations do not undergo Friedel croft acylation Q.54 In the Gattermann Koch synthesis, the electrophile is Θ : C O : C l Θ HCl + AlCl AlCl + H 3 4

19 Q.55 In desulfonation of benzene sulfonic acid, on treatment with steam, electrophile is H SO 3 H 2 O None of these H Q.56 (A); Unknown (A) is

20 Q.57 (B), Product (B) in this reaction is Q.58 Suitable product of this reaction is

21 Q.59 Product (A) of above reaction is In ortho we have intra H bonding Stronger are the intermolecular forces substance is less volatile. Q.60 Compound X, is:

22 All are correct Rearrangement will take place to form 3 carbocation. Q.61 In the given reaction, what is the product? Q.62 Which of the following represents Friedel Crafts reaction? AlCl C H + C H Cl 3 C H C H + HCl ZnCl C H OH+ HCl C6H5 Cl + H2 O AlCl C H Cl + CH COCl C6H5COCH 3 + Cl2 Conceptual ether C H Br + Mg C H MgBr

23 Q.63 The compound X is: None of these Q.64 Arrange the following in decreasing order of reactivity towards EAS (electrophilic aromatic substitution) a b c c b a a c b c a b Heavier isotopes are less reactivity.

24 Q.65 Arrange the following in decreasing order of rate of Nitration. b c a d e d e a = c b d a = c e b a c b e d c a because heavier isotopes are less reactive. e c a (Pulling group) Q.66 Consider the following statements I : Hyperconjugation helps in increasing electron density at ortho and para sites in case of alkyl groups. II : Electron donating groups are activators and ortho and para directors because they stabilize the arenium cations. III : Electron withdrawing groups are activators and are meta directors because they stabilize the arenium cations. IV : Halogens are activators and ortho and para directors. Select correct statements I, II I, II, III II, III, IV I, IV Conceptual Q.67 Arrange these groups in decreasing order of their electron donating power in resonance OH, O CO CH, NH NO 3 2 I II III IV III I II IV II I III IV III II I IV I III II IV NH 2 after donating becomes = NH2 OH after donating becomes =OH N O Stability

25 Q.68 In electrophilic aromatic substitution reaction, a phenyl substituent on the aromatic ring is A deactivator and m director A deactivator and o, p director An activator and m director An activator and o, p director Correct Answer 4 For EAS, phenyl is an activator and o, p director. Q.69 In electrophilic aromatic substitution reactions a N=O substituent on the aromatic ring is A deactivator and m director A deactivator and o, p director An activator and m director An activator and o, p director N=O is weakly deactivating o, p director Q.70 Which of the following is not the activating group? F Correct Answer 4 F is weakly deactivating. Q.71 Which of the following is a correct comparison of rate of electrophilic substitution (bromination)? ri rii ri rii r I = rii None of these (More no. of Hyperconjugation in I than II)

26 Q.72 Which xylene gives only one monochloro derivative by electrophilic aromatic substitution? p xylene m xylene o xylene None of these Both (a) and (b) will give only one monochloro derivative. Q.73 The correct decreasing order of relative reactivity with E + is Aniline acetanilide benzene acetophenone Aniline acetanilide acetophenone benzene Aniline benzene acetanilide acetophenone benzene acetophenone acetanilide aniline Q.74 Which of the following undergoes electrophilic substitution reaction (nitration), the fastest? Toluene Benzene Benzoic acid Nitrobenzene Toluene Q.75 The correct decreasing order of relative reactivity with E + is p HOOC C6H4 COOH p CH3C6H4COOH C6H5CH 3 p CH3C6H4CH3 p CH3C6H4CH 3 C6H5CH 3 p CH3C6H4COOH p H OOC C6H4 COOH C6H5CH 3 p CH3C6H4CH 3 p CH3C6H4COOH p HOOC C6H4 COOH p CH3C6H4COOH C6H5CH 3 p CH3C6H4CH 3 p HOOC C6H4 COOH p CH C H CH C H CH p CH C H COOH p HOOC C H COOH

27 Q.76 Be n zen e o rth o chlo ro nitro b en zene For the conversion, which of the following sequences is the most appropriate? Chlorination, then nitration Nitration then chlorination Chlorination, sulphonation, nitration, desulphonation Nitration, sulphonation, chlorination, desulphonation Q.77 Product of this reaction on mono nitration is Q.78 Which of the following compounds will undergo bromination most rapidly using Br 2, FeBr 3? p methylacetanilide Bromobenzene Acetanilide Benzenesulphonic acid p methylacetanilide acetanilide bromo benzene benzenesulphonic acid

28 Q.79 Identify the correct order of reactivity in electrophilic substitution reactions of the following compounds I II III IV IV III II I II I III IV II III I IV II I III IV (on the basic of +I / donating groups) Q.80 Arrange the following compounds in the order of increasing tendency to undergo electrophilic substitution Q.81 The major product on the monobromination (with Br 2 /FeBr 3 ) of the following compound A is

29 Q.82 The order of decreasing reactivity towards an electrophilic reagent, for the following (1) Benzene (2) Toluene (3) Chlorobenzene (4) Phenol would be Correct Answer

30 Q.83 The compound B is Q.84 Which one of the following compounds give only one isomer upon nitration?

31 Q.85 Consider the following compound The relative reactivity towards halonium ion is such that: I II III II I III II III I III I II II I III Q.86

32 No reaction Q.87 The major product obtained in the reaction is expected to be: Q.88 The order of reactivity of the following compounds

33 Towards electrophilic substitution will be: I II III IV IV III II I II I III IV III II I IV I II III IV (Hyperconjugation) Q.89 In the following reaction The structure of major product X is: Para position to electron donating group Q.90 Arrange the following groups in order of decreasing o and p directing strength: Correct Answer 4

34 Q.91 Which of the following compounds undergoes nitration at fastest rate? Q.92 Rank the following compounds in decreasing order of reactivity in electrophilic aromatic substitution reaction: In (3), O and N both are donations. (1), O is donation. (2), O withdrawing.

35 Q.93 Which of the following is the major product from the sulphonation of tetralone? Q.94 Which of the following is the major product from bromination of meta nitrobenzene sulphonic acid?

36 (meto to both SO 3 H and NO 2 ) Q.95 Gammexane can be obtained from benzene with reagent Br 2, sunlight Cl 2, sunlight Cl 2, CCl 4 COCl 2, anhydrous AlCl 3 Q.96 Which of the following cannot be oxidized to benzoic acid on treatment with KMnO 4, H?

37 Correct Answer 4 Because no hydrogen. Q.97 C 6 H 5 Cl Ortho C 6 H 4 Cl 2 C 6 H 6 Cl 6 Para C 6 H 4 Cl 2 C 6 H 6 Cl 6 The product of following reaction is C H + Cl hv 6 6 2? Q.98 Which of the following will be obtained by the bromination of ethylbenze in presence of light? Correct Answer 4

38 Q.99 Q.100 Which sequence of steps describes the best synthesis of compound

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