الرحيم الرحمن الله بسم

Organic Chemistry II

KEY

Final Exam Review QuestionsBy Dr. Mohammad A. R. IsmaielCollege of Science for Women

Babylon UniversityThanks for the Dean of the College

Examples of the types of questions you can expect to see on the final

1. The IUPAC name for the formula CH3CH2CH2CHOHCH=CH2 is

1. 5-hexene-3-ol 2. 1-hexene-3-ol2. 1-hexene-5-ol 4. n-propyl ally alcohol5. allyl n-butyl ether

2. What is the order of reactivity toward SN2 displacement in the following series?

A. B. C.

1. A>B>C 2. A>C>B3. B>A>C 4. B>C>A5. C>A>B

3. The principal organic product formed in the reaction below is

1. CH3CHBr(CH2)8COOH 2. CH2BrCH2(CH2)8COOH

3. CH2=CH(CH2)8COBr 4. CH2=CH(CH2)7CHBrCOOH

5. none of these

4. Treatment of with HCl gives

1. 2.

3. 4.

5.

5. A compound which is insoluble in cold, concentrated sulfuric acid is

1. n-hexane 2. 1-hexene3. 2-hexyne 4. ethyl acetate5. benzyl alcohol

6. Which reagent would convert cyclohexene into a cis-glycol?

1. sodium tert-butoxide in chloroform2. hydrogen peroxide and aqueous acetic acetic acid3. ozone and moist zinc dust4. periodic acid5. cold dilute potassium permanganate

7. Which statement is correct for an SN1 reaction at a chiral carbon atom?

1. the product will be optically active, but have the opposite configuration2. the reaction will involve racemation3. a carbanion is formed as an intermediate4. the rate of the reaction is a function of the concentration of the nucleophile5. the attacking group will be a strong electrophile

8. Which does NOT involve a carbocation?

1. (CH3)3CCl + AgNO3 2. (CH3)3COH + HCl 3. (CH3)3CH + Cl2 + uv light 4. CH3CH=CHCH2OH + H3O+

9. The reagent which would distinguish between 1-hexyne and 1-hexene is

1. Ag(NH3)2+ 2. KMnO4

3. Br2 in CCl4 4. H2SO4

5. NaOH

10. In methyl alcohol solution, bromine reacts with ethylene (ethene) to yield BrCH2CH2OCH3 in addition to 1,2-dibromoethane because

1. the methyl alcohol solvates the bromine.2. the ion formed initially may react with Br1- or CH3OH.3. this is a free radical reaction.4. the reaction follows Markovnikov’s rule.5. of none of these reasons.

11. The important minor product from the reaction of sodium cyanide with 2-iodopentane in anhydrous acetone is

1. 1-pentene 2. 2-pentene3. pentane 4. 2-pentanol5. 4,5-dimethyloctane

12. The monochloroisomer that predominates in the mixture resulting from the free radical chlorination of CH3CH2CH2CH=CH2 is

1. ClCH2CH2CH2CH=CH2 2. CH3CHClCH2CH=CH2

3. CH3CH2CHClCH=CH2 4. CH3CH2CH2CCl=CH2

5. CH3CH2CH2CH=CHCl

13. When a solid organic compound is recrystallized, the cold filtrate from the cooled mixture is

1. saturated with the compound. 2. an unsaturated solution of the compound.3. entirely free of the compound. 4. pure solvent.5. supersaturated with the compound.

14. Sodium iodide in anhydrous acetone reacts most rapidly with

1. CH3CH2CH2Br 2. (CH3)3CBr 3.

4. CH2=CHBr 5.

15. CH3CH=CHCH2OH reacts with HBr to give which two bromobutenes?

1. CH3CH=CHCH2Br + CH3CH=CBrCH3

2. CH3CH=CHCH2Br + CH3CHBrCH=CH2

3. CH2=CHCH2CH2Br + CH2=CHBrCH=CH2

4. CH2=CBrCH2CH3 + CH2=CHCH2CH2Br

5. BrCH2CH=CHCH3 + BrCH2CH2CH=CH2

16. What is the possible number of stereoisomers having the structure below?

1. two optically active and one meso2. None optically active3. four optically active4. two optically active and two meso5. one optically active and one meso

17. The addition of Br2 to trans-2-butene giving meso-2,3-dibromobutane can be explained by a mechanism involving

1. a free radical. 2. a carbocation.3. a cyclic bromonium ion. 4. a carbanion.5. simultaneous attack by to bromine atoms.

18. Which metal catalyzed reaction would release the greatest amount of heat per CH2 unit?

1. cyclopropane + H2 propane

2. cyclobutane + H2 butane

3. cyclopentane + H2 pentane

4. cyclohexane + H2 hexane

5. cyclododecane + H2 dodecane

19. What is the IUPAC name for the compound shown below?

1. 2,3-dimethyl-4-pentene2. 1,1-dimethyl-2-isopropylethene3. 2,3-dimethyl-2-pentene4. All of the above5. None of the above

20. Which dimethylcyclobutane has two optically forms?

1. trans-1,2- 2. cis-1,2-3. trans-1,3- 4. cis-1,3-5. 1,1-

21. The C-C-N angle in acetonitrile, CH3CN is

1. 45° 2. 60° 3. 109.28°4. 120° 5. 180°

22. Which is NOT characteristic of a free radical chain reaction?

1. It produces a mole of product for a mole of free radical initiated.2. It gives the product derived from the most stable free radical.3. It may be initiated by peroxides.4. It may be initiated by high heat.5. It may be initiated by ultraviolet light.

23. A reaction at a chiral carbon of an optically pure isomer which takes place exclusively by an SN2 reaction, and in which priorities do not change, proceeds with

1. inversion and no racemization.2. inversion and some racemization.3. inversion and complete racemization.4. retention of configuration and some racemization.5. retention of configuration and no racemization.

24. Which would yield 2-methyl-2-pentene when refluxed with zinc dust in alcohol?

1. 2.

3. 4.

5.

25. Which anion is the weakest base?

1. C2H5O1- 2. NO31- 3. CN1-

3. CH3COO1- 5. OH1-

26. Which compound would be the major product when (CH3)2CHCHBrCH2CH3 is treated with alcoholic KOH?

1. (CH3)2CHCH2CHOHCH3 2. (CH3)2CHCHOHCH2CH3

3. (CH3)2COCH2CH2CH3 4. (CH3)2CHCH=CH3

5. (CH3)2C=CHCH2CH3

27. If tert-butyl bromide and sodium amide (NaNH2) react, the product formed is

1. tert-butylamine. (amines are R-NH2)2. tert-butylammonium bromide.3. a mixture of butylamines.4. isobutylene. (2-methylpropene)5. none of these.

28. In the reaction below, the product would be

1. a mixture of diastereomers.2. opticaly active.3. unresolvable.4. a racemate.5. a meso compound.

29. The rate of an SN2 reaction run in a polar aprotic solvent relative to the same reaction in a polar protic solvent would be

1. the same.2. slower.3. faster.4. unpredictable.5. unimolecular.

30. Which of the amines listed below would have the lowest boiling point?

1. CH3CH2CH2NH2 2. CH3CH2NHCH3

3. (CH3)3N 4. (CH3)3CNH2

5. (CH3)2CHNH2

31. Racemic 2,3-dibromobutane can be made by adding bromine to

1. cis-2-butene. 2. 1-butene.3. 1,3-butadiene. 4. trans-2-butene.

32. Which species represents the electrophile in aromatic substitution?

1. :NO2- 2. NO2

+ 3. NO2 4. NO3- 5. SO3H+

33. Which could NOT be prepared directly from 4-bromobenzene-diazonium ion?

1. Phe-Br 2. 4-Br-Phe-Br3. 4-Br-Phe-F 4. 4-Br-Phe-CN5. 4-Br-Phe-COCH3

34. A good starting material for the preparation of 4-chlorobenzenesulfonic acid would be

1. benzenesulfonic acid 2. 1,4-dinitrobenzene3. chlorobenzene 4. 4-chlorobenzioc acid5. 1,4-dichlorobenzene

35. Which represents an intermediate formed in the reaction of toluene and chlorine at elevated temperature in sunlight?

1. 2.

3. 4.

5.

36. The reaction of benzyl chloride with sodium isopropoxide yields

1. benzaldehyde and 2-chloropropane 2. 1,2-diphenylethane and acetone3. acetone and toluene 4. benzyl isopropyl ether5. isopropyl ether and the sodium salt of benzyl alcohol

37. An aromatic hydrocarbon yields a single mononitro derivative. The hydrocarbon is

1. ethylbenzene 2. o-xylene3. propylbenzene 4. naphthalene5. p-xylene

38. Which is the best way to prepare meta-bromoaniline?

1.

2.

3.

4.

5.

39. Which is the principal product when benzaldehyde is allowed to react with propionaldehyde in the presence of dilute aqueous sodium hydroxide at room temperature?

1. 2.

3. 4.

40. Which does NOT represent a Diels-Alder type of reaction?

1. 2.

3. CH2=CHCH=CH2 + CH2=CHCOOH 4. CH3COCH3 + CH3CH=CHCHO

5.

41. Which statement about the aldol condensation is correct?

1. A Lewis acid is commonly used as a catalyst.2. The initial step is probably the formation of a carbanion.3. A Lewis base is employed to induce carbocation formation.4. The carbon chain is lengthened through the elimination of 1 mole of water.

42. Which is the strongest acid in water?

1. Phenol 2. 3-nitrophenol3. 4-aminophenol 4. 4-nitrophenol5. hydroquinone

43. The most direct malonic ester synthesis of 3-phenylpropanoic acid would involve the use of

1. C6H5CH2CH2CH2Cl 2. C6H5CH2CH2Cl3. C6H5CH2Cl 4. C6H5Cl5. ClCH2COOH

44. A compound gives a positive test with I2/NaOH and is extracted from benzene by saturated NaHSO3. It may be

1. CH3(CH2)4CHO 2. CH3(CH2)3COCH3

3. CH3CH2COCH2CH3 4. CH3(CH2)4CH2OH5. CH3(CH2)3)CHOHCH3

45. Which is an L-sugar that on oxidation gives an optically inactive dibasic acid (2 COOH groups)?

1. 2.

3. 4.

5.

46. Select the final product from this sequence of reactions.

1. 2.

3. 4.

5.

47. In the reaction below, the product would be

1. a racemate. 2. optically active.3. a meso compound. 4. a mixture of diastereomers.5. unresolvable.

48. A group which deactivates the benzene ring towards EAS but which directs the incoming group principally to the ortho and para positions is

1. -NH2 2. -Cl3. -NO2 4. -C2H5

5. -NHCOCH3

49. What is true for the equilibrium reaction

1. The use of equimolar quantities of CH3OH and CH3COOH will give the greatest yield of the ester at equilibrium.

2. Removal of water will increase the amount of ester at equilibrium.3. Addition of CH3COOCH3 will cause the formation of equal an equal number of moles of

water.4. Application of pressure increases the amount of ester at equilibrium.5. Changing the catalyst will affect the position of the equilibrium.

50. Which reagent would bring about this transformation?

1. Sn and HCl 2. Zn and HCl3. H2 and Pt 4. LiAlH4 and ether5. Na and alcohol

51. The reaction between carbon dioxide and a Grignard reagent will yield

1. an alkane. 2. an alkylmagnesium halide.3. an alcohol. 4. magnesium carbonate.5. a carboxylic acid.

52. Which is a practical method for the preparation of iodobenzene?

1. iodine + benzene + iron2. iodine + benzene + UV light3. potassium iodide + chlorobenzene4. sodium hypoiodite + benzamide5. potassium iodide + benzenediazonium ion

53. Which reaction sequence would be best to prepare 3-chloroaniline from benzene?

1. chlorination, nitration, reduction 2. nitration, chlorination, reduction3. nitration, reduction, chlorination 4. nitration, chlorination5. nitration, reduction, acetylation, chlorination, hydrolysis

54. The catalyst used in the halogenation of benzene is

1. a proton donor. 2. an electron donor.3. a Lewis base 4. a Lewis acid5. a proton acceptor

55. The reaction of Br2/FeBr3 with benzene to form bromobenzene is know as

1. free radical substitution 2. nucleophilic substitution3. electrophilic substitution 4. ionic addition5. elimination

56. Which reagent will lengthen the carbon chain by two carbons in one step when reacted with an organolithium reagent?

1. acetic acid 2. formaldehyde3. iodomethane 4. ethylene oxide5. ethanol

57. Which aromatic compound behaves most like benzoic acid when it undergoes reaction with concentrated nitric acid and sulfuric acid?

1. Phenol 2. Chlorobenzene3. Phenyl methyl ketone 4. Benzene5. Toluene

58. An explanation of the addition of sodium bisulfite to heptanal and 2-heptanone but not to 3-heptanone is

1. steric inhibition of resonance. 2. steric hinderance.3. steric inhibition of solvation. 4. differences in resonance effects.5. the lower dipole moment of 3-heptanone.

59. Which will undergo a Friedel-Crafts alkylation reaction?

1. a, b, c 2. a and c3. b and d 4. a and b5. c and d

60. The reaction of diethylmalonate with sodium ethoxide produces ethanol and a

1. free radical 2. carbocation3. molecular species 4. carbanion5. carboxylate ion

61. The principal product of the reaction between methyl butanoate and 2 moles of CH3MgBr after hydrolysis is

1. C3H7COCH3 2. C3H7C(OH)(CH3)2

3. C3H7CHOHCH3 4. C3H7COCH(CH3)2

5. C3H7CH2OH

62. Which reaction sequence would be best to prepare 1,4-diaminobenzene from benzene

1. nitration, sulfonation, nitration, hydrolysis, reduction2. nitration, reduction, nitration, reduction3. nitration, reduction, acetylation, nitration, reduction4. nitration, reduction, acetylation, nitration, hydrolysis, reduction5. nitration, reduction

63. The correct name for is

1. 7,9-dichloronaphthalene 2. 3,5- dichloronaphthalene3. 2,4- dichloronaphthalene 4. 1,3- dichloronaphthalene5. 6,8- dichloronaphthalene

64. Which of the following would react most rapidly with sodium ethoxide to produce an ether?

1. chlorobenzene 2. p-nitrotoluene3. p-nitrochlorobenzene 4. m-(chloromethyl)-toluene5. m-chlorotoluene

65. Select the final product from this sequence of reactions.

1. 2.

3. 4.

5.