CLASSIFICATION OF ALKYL HALIDES, ALCOHOLS, THIOLS, ETHERS, AND SULFIDES NOMENCLATURE OF ALKYL HALIDES, ALCOHOLS, THIOLS, ETHERS, AND SULFIDES

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1 Chemistry 262 Winter 2018 Final Exam Practice The following practice contains 44 problems and mimics Monday s 150 point final, which will also contain 44 problems valued at 3.5 points each with approximately ½ of the problems drawn directly from the quarter s homework. It will also contain 2 unknown analysis problems valued at 6 points/question. Apologies for the repeats Name CLASSIFICATIN F ALKYL ALIDES, ALCLS, TILS, ETERS, AND SULFIDES 1. Neopentyl alcohol is classified as a a. 1 o alcohol 2 o alcohol c. 3 o alcohol 4 o alcohol e. None of the above NMENCLATURE F ALKYL ALIDES, ALCLS, TILS, ETERS, AND SULFIDES 2. What is the correct IUPAC name for the following compound? a. 1,2-Butanediol Isopropanol c. 1-Propanol 1,2-Propanediol e. Propylene glycol

2 MGENEUS INTERMLECULAR INTERACTINS BILING PINTS AND MELTING PINTS 3. Which of the following would have the greatest boiling point? a. Benzene Cyclohexene c. exanoic acid Ethylene glycol e. Sodium acetate MGENEUS INTERMLECULAR INTERACTINS YDRGEN BNDING 4. Which of the following compounds has the lowest boiling point? C 2 I II III IV V e. V ETERGENEUS INTERMLECULAR INTERACTINS SLUTINS AND SLUBILITY 5. In which of the following solvents would anhydrous MgS 4 be completely insoluble? a. Water Tetrahydrofuran c. Dimethyl formamide Dimethyl sulfoxide e. exane ETERGENEUS INTERMLECULAR INTERACTINS SLUTINS AND SLUBILITY 6. Which of the following compounds would have the greatest solubility in water? a. Diethyl ether Methyl propyl ether c. 1-Butanol 1,2-Butanediol e. 4-Mercapto-1-butanol

3 NUCLEPILIC SUBSTITUTIN AND -ELIMINATIN REACTINS REACTIN RATES 7. Consider the reaction of 2-iodopentane with acetate. Assuming no other changes to the system, what effect on the rate would result from simultaneously doubling the concentrations of both 2-iodopentane and acetate? I Na NaI a. No effect The rate would double (2x) c. The rate would triple (3x) The rate would increase 4 fold (4x) e. The rate would increase 6 fold (6x) NUCLEPILIC SUBSTITUTIN AND -ELIMINATIN REACTINS TRANSITIN STATE TERY 8. Which of the following is true for any nucleophilic substitution reaction? a. > 0 < 0 c. G > 0 G > 0 e. G < 0 NUCLEPILIC SUBSTITUTIN AND -ELIMINATIN REACTINS TE S N 2 REACTIN 9. When 0.10 mol of IC 2 C 2 C 2 C 2 Cl reacts with 0.10 mol of NaC 3 at 40 o C, the major product formed is a. C 3 C 2 C 2 C 2 C 2 Cl C 3 C 2 C 2 C 2 C 2 I c. C 3 C 2 C 2 C 2 C 2 C 3 C 2 =CC 2 C 2 Cl e. C 2 =CC 2 C 2 I

4 NUCLEPILIC SUBSTITUTIN AND -ELIMINATIN REACTINS STERECEMISTRY 10. What would be the major product(s) of the following reaction? C 2 Cl C 3 S N 2 3 C C 2 C 3 C 2 I II C 2 Cl C 3 III e. More than one of the above IV C 2 Cl NUCLEPILIC SUBSTITUTIN AND -ELIMINATIN REACTINS CRITICAL FACTRS 11. Which of the following is the strongest nucleophile in an aprotic solvent such as dimethylsulfoxide? c. Cl F e. All are equally nucleophilic in this environment

5 NUCLEPILIC SUBSTITUTIN AND -ELIMINATIN REACTINS E2 REGICEMISTRY 12. What is the principal product of the following reaction sequence? a. 1. t-buk, t-bu 2. 2, Pd/C, Et c. t-bu e. None of the above represents a significant product NUCLEPILIC SUBSTITUTIN AND -ELIMINATIN REACTINS E2 STERECEMISTRY 13. What is major product of the following reaction? Et, EtNa a. heat Et c. e.

6 NUCLEPILIC SUBSTITUTIN AND -ELIMINATIN REACTINS FACTRS INFLUENCING S N 1 AND E1 REACTINS 14. Which statement(s) is/are true of acid-catalyzed alcohol dehydrations? a. Protonation of the alcohol is a fast step Formation of a carbocation from the protonated alcohol is a slow step c. Rearrangements of less stable carbocations to more stable carbocations are common Loss of a proton by the carbocation is a fast step e. All of the above NUCLEPILIC SUBSTITUTIN AND -ELIMINATIN REACTINS GENERAL PRDUCT PREDICTINS 15. What are the principal products formed when 2-bromo-2-methylpentane reacts with sodium propynide? C: Na? I II III C C C C e. V IV V

7 NUCLEPILIC SUBSTITUTIN AND -ELIMINATIN REACTINS GENERAL PRDUCT PREDICTINS 16. What would be the major product outcome for the following reaction? 3 C C 25 o C 3 C 3 C CN CN I II 3 C CN 3 C NC III IV e. Equal amounts of I and III RGANMETALLIC CMPUNDS FRMATIN F GRIGNARD AND RGANLITIUM REAGENTS 17. Which of the following is the correct order of capacity towards Grignard formation, from easiest to hardest? R RCl RI RF I II III IV, II, III, IV I, I, II, IV c. IV, II, I, III III, I, IV, II e. I, IV, III, II

8 RGANMETALLIC CMPUNDS REACTINS F GRIGNARD AND RGANLITIUM REAGENTS 18. Which of the following reactions will not produce a primary alcohol? a. (C 3 ) 2 CC 2 C 2 C 1. LiAl 4 /Et C 2 C 2 c. (C 3 ) 2 CC 2 C 2 Mg 1. NaB e. C 6 5 CC C 3 C 2 C 2 C 2 Li 1. 2 C= C 3 (C 2 ) 5 C 1. LiAl 4, Et

9 CARBENES, CARBENIDS, AND TE SIMMNS-SMIT REACTIN 19. What is the major product for the following reaction I 2 C 2 a. I I Zn(Cu) c. I e. More than one of the above ALCL AND TIL ACID BASE CNSIDERATINS 20. Which of the following has the lowest pk a value in aqueous solution? a. Mercaptoethane Phenol c. Phenyl mercaptan tert-butyl alcohol e. 1,2-ethanediol DEYDRATIN F ALCLS 21. Carbocations are frequently intermediates in acidic reactions of alkenes, alcohols, etc. Which of the following is a common carbocation property? a. Rearrangement to a more stable carbocation Loss of a proton to form an alkene c. Combination with a nucleophile Reaction with an alkene to form a larger carbocation e. All of the above

10 REACTIN F ALCLS WIT YDRGEN ALIDES 22. Which of the following could be used to synthesize 2-chlorobutane? a. C 3 C 2 C C 2 + Cl 2 (aq) C 3 C 2 CC 3 + Cl c. C 3 C 2 C C + Cl C 3 C 2 C C + Cl 2 e. None of the above BASE CMPATABLE ALCL-DERIVED LEAVING GRUPS 23. What would be the principal product outcome of the following reaction sequence? pc 3 C 6 4 S 2 Cl base tosylate Na ethanol? C 3 S 2 C 6 4 C 3 C 3 C 3 C 3 I II III IV e. An equimolar ratio of II & III C 3 MDERN METDS FR CNVERSIN F ALCLS T ALKYL ALIDES 24. Which reagent(s) would transform propyl alcohol into propyl bromide? a. Conc. / P 3 c. Na (aq) / Two of the above e. All of the above

11 RGANIC REDX REACTINS 25. Which of the following is the correct order of decreasing level of oxidation? C 2 Cl 2 C C 3 I II III, II, III II, II, I, III, I c. II, I, III I, III, II XIDATIN F ALCLS 26. Cr 3 in 2 S 4 / 2 will fail to give a positive test with which of these compounds? a. C 3 C 2 C 2 C 2 C 3 CC 2 C 3 c. (C 3 ) 3 C C 3 C 2 C 2 C e. All give a positive test with Jone s reagent CTET EXPANSIN AND XIDATIN F TILS 27. Which of the following would oxidize a thiol to a sulfonic acid? a. KMn 4 N 3 c. Cl Two of the above e. All of the above

12 SYNTESIS F ALCLS 28. Which product(s) are the expected outcome of the following reaction sequence? C 3 1. B 3 -TF , Na? C 3 C 3 C 3 3 C C 2 + enantiomer + enantiomer + enantiomer I II III IV V e. V INFRARED SPECTRSCPY 29. An optically active compound of molecular formula C 7 12, reacts with cold, dilute KMn 4 and gives a characteristic IR band around 3300 cm -1. n catalytic hydrogenation a new optically active compound is formed, with a formula C Which of the following compounds is a possible candidate? I II III IV V e. V

13 1 -NMR SPECTRSCPY NUMBER F RADIFREQUENCY ABSRPTINS 30. Assuming all are resolved, how many different signals would be observed in the 1 -NMR of the following compound? a. 1 2 c. 3 4 e NMR SPECTRSCPY SPIN CUPLING AND CEMICAL EQUIVALENCY 31. Predict the splitting pattern you would observe for the proton at C1 of 2,3-dimethyl-2- phenylbutane a. Singlet Doublet c. Quartet Septet e. ctet 1 -NMR SPECTRSCPY DESIELDING AND SPIN CUPLING 32. Which of the following best represents the approximate predicted chemical shift and coupling for the hydrogen indicated with the arrow? a. 1.0 ppm, quartet 2.4 ppm, singlet c. 2.4 ppm, triplet 2.4 ppm, quartet e. 3.0 ppm, quartet

14 13 C-NMR SPECTRSCPY CEMICAL EQUIVALENCY, NUMBER F SIGNALS, AND DESIELDING 33. In 13 C-NMR spectroscopy, which of the following functional groups gives rise to the signal furthest downfield? a. C N C c. C C X e. C C 13 C-NMR SPECTRSCPY CEMICAL EQUIVALENCY AND 13 C VS 1 ABSRPTINS CMPARED 34. Assuming all peaks are resolved, which of the following would give rise to 4 peaks in both the 1 -NMR and broadband decoupled 13 C-NMR spectra? I II III IV e. More than one of the above MASS SPECTRMETRY BASIC DEFINITINS AND FRAGEMENTATIN 35. Which of the following C 6 14 compounds would give an MS base peak of m/z = 43? a. C 3 C 2 C 2 C 2 C 2 C 3 (C 3 C 2 ) 2 CC 3 c. (C 3 ) 3 CC 2 C 3 (C 3 ) 2 CC(C 3 ) 2 e. None of these

15 MASS SPECTRMETRY BASIC DEFINITINS AND FRAGEMENTATIN 36. The data below for the isotope envelope of the molecular ion region of a halogen containing species are consistent with the presence of what halogens for the compound in question? M +, I = % M + + 2, I = 64.0 % M + + 4, I = 10.0 % a. 1 1 Cl c. 1, 1 Cl 2 e. 2 Cl SYNTESIS F ETERS AND SULFIDES 37. What is the major product for the following reaction? 2, C 3 a. + enantiomer C 3 + enantiomer c. + enantiomer 3 C C 3 + enantiomer e. More than one of the above

16 SYNTESIS F EPXIDES 38. If cis-2-butene is treated with meta-chloroperbenzoic acid, what is the final product? C 3 3 C 3 C C 3 3 C 3 C 3 C 2 C I II III IV e. None of the above EPXIDES NUCLEPILIC SUBSTITUTIN REACTINS 39. Which of the following is the principal product for the following reaction? C 3 C C 2 A 2 18? a. C 3 C 2 C 2 18 C 3 CC 3 18 c. C 3 CC 2 18 C 3 C C 2 e. 18 C 3 CC

17 EPXIDES NUCLEPILIC SUBSTITUTIN REACTINS 40. Which of the following is the principal product for the following reaction? C 3 - C 3 3 +? C 3 C 3 C 3 C 3 I II III IV e. Equal amounts of II & IV ALKYNES BASIC STRUCTURE AND NMENCLATURE 41. What is the IUPAC name for the compound shown? Cl a. (S,E)-3-chlorohex-4-en-1-yne (R,E)-3-chlorohex-2-en-5-yne c. (S,E)-3-chlorohex-2-en-5-yne (R,E)-3-chlorohex-4-en-1-yne e. (R,E)-3-chloropent-4-en-1-yne ALKYNES ADDITIN REACTINS 42. Addition of excess Cl to 2-methyl-3-heptyne produces a. 2-methyl-3,3-dichloroheptane 2-methyl-2,3-dichloroheptane c. 2-methyl-4,4-dichloroheptane 2-methyl-3,4-dichloroheptane e. 2-methyl-3-chloroheptene f. More than one of the above

18 ALKYNES ADDITIN REACTINS 43. What is the major product for the following reaction sequence? 1. 2, Lindlars catalyst 2. 2, CCl 4 a. + enantiomer + enantiomer c. + enantiomer + enantiomer e. ALKYNES REACTINS F TERMINAL ALKYNES 44. Which of the following would not be a successful method for preparing 5- methyl-1-hexyne a. 1) NaN 2 (2 mol), liq N 3 2) N 4 + C CNa + Cl c. Li + C C 1) NaN 2 (3 mol), liq N 3 + 2) N 4 e. 1) NaN 2 (3 mol), liq N 3 2) N 4 +