CHEM 242 ETHERS, EPOXIDES, AND SULFIDES CHAP 17 ASSIGN

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1 CHEM 242 ETHERS, EPOXIDES, AND SULFIDES CHAP 17 ASSIGN 1. Which of the following is the correct name of the compound below? A) benzyl ethyl ether B) ethyl phenyl ether C) ethylbenzene ether D) ethoxy phenoxy ether 2. The name of the following ether is A) butyl isopropyl ether. B) sec-butyl isopropyl ether. C) isobutyl propyl ether. D) butyl propyl ether. 3. The IUPAC name of the following epoxide is A) cis-2-ethyl-3-methyloxirane. B) trans-2-ethyl-3-methyloxirane. C) trans-1-ethyl-2-methyloxycyclopropane. D) trans-1-ethyl-2-methylethane epoxide. 4. Consider the three compounds below. I. CH 3CH 2OCH 2CH 3 II. CH 3CH 2CH 2CH 2CH 3 III. CH 3CH 2CH 2CH 2OH The two most similar in boiling point are and the two most similar in solubility in water are. A) I and III, II and III B) II and III, I and II C) I and II, I and III D) I and III, I and III 5. The role of 18-crown-6 in the reaction shown below is to A) complex F by ion-dipole attraction and make it more nucleophilic. B) remove Br by ion-dipole attraction and shift the equilibrium to the products. C) complex K + by ion-dipole attraction increasing the solubility of KF and the nucleophilicity of F. D) stabilize the carbocation in the substitution reaction. 6. Which of the following yields an epoxide on treatment with NaOH? A) cis-2-bromocyclohexanol B) cis-1,2-cyclohexanediol C) trans-2-bromocyclohexanol D) 3-bromocyclohexene 1 P a g e

2 7. What is the product of the following reaction? 8. Which of the following is not a good method to make tert-butyl methyl ether? 9. Which one of the following reactions makes the cyclic ether shown below? 10. What is the product of the following reaction? A) (S)-1,2-propanediol B) racemic mixture of 1,2-propanediol C) (R)-1,2-propanediol D) 1,3-propanediol 2 P a g e

3 11. What are the products of the reaction below? 12. What is the product of the following sequence of reactions? 13. What reagents and/or reaction sequence below would convert cis-3-hexene to meso-3,4-hexanediol? A) OsO 4, (CH 3) 3COOH, (CH 3) 3COH, NaOH B) B 2H 6/diglyme followed by H 2O 2/NaOH C) O 3 followed by Zn/H 2O D) CH 3CO 3H followed by NaOH/H 2O 14. Which of the following epoxides is formed when KOH is added to the optically active halohydrin shown below? A) trans-(2s,3s)-2,3-dimethyloxirane B) trans-(2r,3r)-2,3-dimethyloxirane C) 2,2-dimethyloxirane D) meso-2,3-dimethyloxirane 3 P a g e

4 15. What is the final product of the following sequence of reactions? 16. Which of the followings reagents would be used to carry out the reaction shown below? A) CH 3OH, CH 3O - Na + B) CH 3MgBr/ether followed by H 3O + C) CH 3OH, H 2SO 4 D) H 2O/H 2SO 4 followed by CH 3OH 17. What is the major product of the following nucleophilic ring-opening reaction? 18. Ethylene glycol reacts in acid to form a cyclic compound with the formula of C 4H 8O 2. Which one of the following is this cyclic compound? 4 P a g e

5 19. What is the product of the reaction shown below? 20. What product would result from: 21. Which of the following ethers could NOT be made efficiently using the Williamson ether synthesis? 22. What results when dimethylsulfide is treated with sodium periodate? 5 P a g e

6 23. What results when dimethylsulfide is treated with methyl iodide? 24. Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between A) AgNO 3 in alcohol B) NaOH in H 2O C) Br 2 in CCl 4 D) Cold concd. H 2SO 4 E) KMnO 4 in H 2O O and? 25. Which of these ethers is most resistant to peroxide formation on exposure to atmospheric oxygen? A) CH 3OCH 2CH 3 B) CH 3CH 2OCH 2CH 3 C) (CH 3) 2CHOCH(CH 3) 2 D) (CH 3) 2CHOCH 2CH 3 E) CH 3OC(CH 3) Which of these ethers is least likely to undergo significant cleavage by hot aqueous H 2SO 4? CH 3 OCH 3 CH 3 OCH(CH 3 ) 2 (CH 3 ) 2 CHOCH(CH 3 ) 2 I II III (CH 3 ) 3 COC(CH 3 ) 3 O IV A) I B) II C) III D) IV E) V V 27. When 3-methyl-2-pentene is treated with mercuric acetate, Hg(O 2CCH 3) 2, in a THF-ethanol mixture and the resulting product reacted with NaBH 4 in basic solution, the principal product formed is which of these? A) 3-methyl-3-pentanol B) 3-ethoxy-3-methylpentane C) 3-methyl-2-pentanol D) 2-ethoxy-3-methylpentane E) 1-ethoxy-3-methylpentane 6 P a g e

7 28. Which is the best method to prepare 2-ethoxy-5methylhexane? A) C 2H 5ONa + (CH 3) 2CHCH 2CH 2Br B) C 2H 5ONa + (CH 3) 2CHCH 2CH 2CH 2CH 2Br C) C 2H 5ONa + (CH 3) 2CHCH 2CH 2CHBrCH 3 D) C 2H 5Br + (CH 3) 2CHCH 2CH 2CH(CH 3)ONa E) C 2H 5OH + (CH 3) 2CHCH 2CH 2CHOHCH 3 + H 2SO 4, 140 C 29. What is the most accurate name for the molecule represented by the following Fischer projection formula? A) sec-butyl methyl ether B) Isobutyl methyl ether C) tert-butyl methyl ether D) (R)-2-Methoxybutane E) (S)-2-Methoxybutane H H 3 CH 2 C OCH 3 CH 3 NAME DATE ANSWER SHEET CHEM 242 CHAP 17 ASSIGN SPRING P a g e

Exam 2 Chem 109a Fall 2004

Exam 2 Chem 109a Fall 2004 Please put your name and perm number on both the exam and the scantron sheet. Next, answer the following 34 multiple-choice questions on the scantron sheet. Then choose one A-type