4th Non-Departmental Exam Questionnaire no: I. Multiple Choice.

Write the CAPITAL LETTER which corresponds to the BEST answer on the space between H and K in the separate answer sheet. (1 point each) I. The most reactive compound in an SN2 reaction.

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2. The worst leaving group in an elimination reaction.

3. The best nucleophile in a substitution reaction at a primary carbon. A B C D

4. The most reactive compound in a SN1 reaction.

For # 5, consider the pair of reactions below to answer the question/s. Reaction A:

5. Refer to Reaction A. The mechanism for these reactions is: A. SN1 C. E1 B. SN2 D. E2 For #s 6-7, consider the pair of reactions below to answer the question/s. Reaction N:

6. The kinetics of these reactions are: A. second-order B. first-order in nucleophile 7. Water is what type of solvent? A. nonpolar aprotic B. polar aprotic

C. not measurable D. first-order in alkyl halide C. polar protic D. nonpolar protic

For #s 8-10, consider the pair of reactions below to answer the questions. Reaction J:

8. Which reaction above is faster? Explain your answer. 9. Doubling the concentration of potassium hydroxide in these reactions: A. causes the reaction mechanism to change C. Has no effect on the rate of reaction B. halves the rate of reaction D. doubles the rate of reaction
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10. The mechanism for these reactions is: A. SN2 B. E2

C. SN1 D. E1

For #s 11-13, consider the pair of reactions below to answer the questions. Reaction E:

11. The substrate in the reaction is: 12. Compound B is the: A. SN2 Product B. E2 Product 13. Compound C is the: A. SN2 Product B. E2 Product C. SN1 Product D. E1 Product C. SN1 Product D. E1 Product

#14-16. For each substrate below, choose which reaction type is favored. A. SN1 C. E1 B. SN2 D. E2 14. Reaction L 15. 16. Reaction Y Reaction N

17. Hydrolysis of neutral compound A, C5H10O2, gave an acid B and an alcohol C. C reacted with PCl3, and was then treated with Mg. Addition of CO2 followed by hydrolysis, yielded an acid identical to B. What is compound A? A. ethyl propanoate C. propyl acetate B. methyl butanoate D. pentanal 18. Compound A, C5H10, decolorized a solution of Br2 in CCl4. When it was dissolved in cold, concentrated sulfuric acid and then heated with water, B resulted. B, (C5H12O) reacted with chromic acid to give C (C5H10O). Both B and C gave positive iodoform tests. The reaction mixture of the iodoform tests also produced isobutyric acid. Determine the identity of A. A. 3-methyl-2-butene C. methyl isopropyl ketone B. 3-methyl-2-butanol D. 2-methyl-2-butene 19. The iodoform reaction may be used to distinguish between the following pairs of compounds: A. acetoacetone and acetaldehyde C. ethanal and propanal B. propanal and propanol D. 2-propanol and 2-propanone 20. What alkyl halide (if any) would yield purely 2-pentene upon Dehydrohalogenation? A. 2-pentylchloride C. 3-pentylchloride B. 1-pentylchloride D. none 21. The major product expected from the Dehydrohalogenation of 2-bromohexane is A. Z-2-hexene C. E-2-hexene B. 1-hexene D. all of the above 22. ____ is the most reactive towards Esterification. A. HCOOH B. CH3COOH 23. ____ is the most susceptible towards Nu- addition. A. 2-methylpropanal B. CH3CH2C(=O)CH3 24. Most reactive towards HBr... A. phenylmethanol B. (4-nitrophenyl)methanol C. CH3CH2COOH D. CH3CH(CH3)COOH C. p-nitrobenzaldehyde D. methyl phenyl ketone C. (4-hydroxyphenyl)methanol D. (4-methylphenyl)methanol

25.Best reagents for the conversion of cyclohexanol to methylcycohexene: A. C.

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B.

D.

26. Most easily hydrolyzed in H2O A. benzoic acid B. benzoyl chloride

C. p-nitrobenzoyl chloride D. p-nitrobenzoic acid

27. An unknown compound gave a positive Tollens test. Treatment of the unknown with I2/NaOH gave a solid, which was identified as iodoform. Which of the following is the unknown compound? A. C. B. D.

28. All of the following give carboxylic acid when hydrolyzed except A. Nitrile C. Ketal B. Ester D. Anhydride 29. The product of the reaction of A. B. + NaOH (aq) is: C. D.

30. Which of the following will not react with NaOH? A. benzoic acid B. phenol

C. propyne D. methylmagnesium bromide

31. Which SN1 reaction of each pair would you expect to take place more rapidly? A. (CH3)3CCl (1.0 M) + CH3CH2O- (2.0 M) B. CH3)3CCl (2.0 M) + CH3CH2O- (1.0 M) 32. Which SN2 reaction of each pair would you expect to take place more rapidly? A. CH3CH2Br (1.0 M) + CH3O- (1.0 M) B. CH3CH2Br (1.0 M) + CH3O- (2.0 M) 33. Which compound will most readily react with an enolate? A. phenol C. water B. phenoxide D. hydroxide For #s 34-36, Determine whether the chiral center will undergo A. Retention of Configuration B. Inversion of Configuration C. Racemization 34. 35. 36.

37. Which of the following reactions will produce an alcohol as a product? A. Acid-catalyzed hydrolysis of ketals C. Reaction of aldehydes with H2O B. Reaction of ketones with NaBH4, H2O D. A and B only 38. Which of the following will yield a carboxylic acid? A. reaction of an acyl chloride with water B. Acid-catalyzed hydrolysis of ester
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C. Reaction of Grignard reagent with CO2, then H+ D. All of these For #s 39-41, What organo metal would yield to the following synthetic products? A. Organo Cu B. Organo Zn C. Organo Li 39. 40. 41. For #s 42-46: Which of the following named reactions would produce the following compounds: A. Williamson Synthesis B. Wittig reaction C. Hoffman Degradation D. Cannizzaro Reaction E. Clemmensen Reduction 42. 43. 46. A. B. C. D. 44. 45.

47. A. B. 48. A. B. 49. A. B. 50. A. B. C. D. C. D. C. D. C. D.

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