CH 3 CH 2 C=CCH 2 CH 3 CH 2 CH 2 OH

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1 CHE 325 ALCOLS, DIOLS, AND THIOLS CHAP 15 ASSIGN 1. What is the correct IUPAC name for the following compound? CH 2 C=CCH 2 CH 2 CH 2 A. 3-methyl-4-ethyl-3-hexen-6-ol B. 4-ethyl-3-methyl-3,6-hexenol C. 3-ethyl-4-methyl-3-hexen-1-ol D. 3-methyl-4-(2-hydroxyethyl)-3-hexene E. 3-(2-hydroxyethyl)- 3-methyl-3-hexene 2. The major industrial process in use today for the production of methanol is the: A. hydration of ethyne. B. distillation of wood. C. hydrogenation of carbon dioxide. D. reduction of methanal. E. catalytic reduction of carbon monoxide. 3. Which of the following reagents might serve as the basis for a simple chemical test that would distinguish between pure 1-butene and CH 2CH 2CH 2? A. Bromine in carbon tetrachloride B. Dilute aqueous potassium permanganate C. Chromic oxide in aqueous sulfuric acid D. All of these E. None of these 4. Which compound would have the highest boiling point? A. CH 2CH 2 B. CH 2O C. CH 2CH 2 D. () 2CH E. HOCH 2CH 2 5. What is the product of the following reaction? 6. Which one of the following is not readily oxidized by K 2Cr 2O 7 in H 2SO 4/H 2O? A. 1-butanol B. sec-butyl alcohol C. 2-methyl-1-propanol D. 2-methyl-2-butanol 7. Which one of the following diols would cleave into two fragments with HIO 4? A. 1,3-hexanediol B. 2,4-hexanediol C. 3,4-hexanediol D. 1,6-hexanediol 8. Identify the reagent needed to carry out the following conversion. A. K 2Cr 2O 7, H 2SO 4/H 2O B. PCC/CH 2Cl 2 C. OsO 4, () 3CO, () 3C, - D. Na 2Cr 2O 7/H 2SO 4 / H 2O E. NaBH 4 F. LiAlH 4 1

2 9. Compound A, C 6H 12O, is readily oxidized with K 2Cr 2O 7 in H 2SO 4/H 2O to give compound B, C 6H 10O. Compound B has four peaks in its C-13 NMR (broadband decoupled). Which one of the following fits the data for compound A? 10. The alcohol product(s) of the reduction of 2-methyl-3-pentanone with LiAlH 4 is(are) A. a single enantiomer. B. a racemic mixture. C. two diastereomers. D. two constitutional isomers. 11. Which of the following syntheses gives 3-methyl-1-hexanol? 12. Which of the following reagents will convert cyclohexene into cis-1,2-cyclohexanediol? A. OsO 4, () 3CO, () 3C, B. HIO 4 C. O 3 followed by Zn/H 2O D. CO 3H (peroxyacetic acid) 13. What is the product of the following reaction sequence? A. cyclopentene oxide B. cyclopentene C. cyclopentane D. cis-1,2-cyclopentanediol 14. To which side, if any, would the reaction below lie? A. to the right B. to the left C. equally to both sides D. this reaction cannot occur 2

3 15. Which of the following is the ester formed between methanol and nitric acid, HNO 3? 16. The lithium aluminum hydride reduction of this ester would yield: O O 1. LiAlH 4 2. H 2 O? 17. What product(s) would you expect from the following reaction? 18. Which one of the following reaction steps work best to carry out the transformation shown below? 19. What is the product of the synthetic sequence below? 3

4 20. Which of the following would be true of the reaction shown? A. A carbon is oxidized in this reaction. B. A carbon is reduced in this reaction. C. The bromine is oxidized in this reaction. D. The bromine is reduced in this reaction. E. This cannot be considered as an oxidation/reduction reaction. 21. Which of the following reactions would you expect to produce 2-pentanol? A. B. C. D. All of these reactions would produce 2-pentanol. E. Only two of these reactions would produce 2-pentanol. Which ones? 22. What is the major product of the following reaction? 23. What reagents would you use to carry out the following reaction? 24. Which of the following would NOT efficiently accomplish the reaction shown? A. NaH B. Na (metal) C. NH 2 D. K (metal) E. 25. What is the final product of the following reactions? A. 2,3-dimethyl-3-pentanol B. 2,3-dimethyl-2-pentanol C. 2,4-dimethyl-3-pentanol D. 2,2-dimethyl-3-pentanol 4

5 26. Predict the major product of the following reaction. A B C D E 27. Which of the following reactions could be used to make cyclohexanecarbonitrile from cyclohexanol? Two of these would work. Which ones? 28. If the following reaction proceeds as indicated, what mechanistic pathway does it most likely follow? A. E2 B. E1 C. S N2 D. S N1 E. free-radical halogenation 29. What major product would you expect from the following reaction? 30. Which of the alcohols listed below would you expect to react most rapidly with HBr? A. CH 2CH 2CH 2CH 2CH 2 B. (CH 2) 2CH 2CH 2 C. (CH 2) 2CH D. CH 2CH 2CH 2CH 2 E. (CH 2) 2C() 5

6 31. Predict the major product of the following reaction. 32. Which would be the best way to carry out the following synthesis? CH 2 CH? CH 2 CH 2 CH 2 A. (1) HA, heat; (2) H 3O +, H 2O, heat B. (1) () 3COK / () 3C; (2) BH 3:THF, then H 2O 2, - C. (1) () 3COK / () 3C; (2) H 3O +, then H 2O, heat D. (1) K, C 2H 5; (2) BH 3:THF, then H 2O 2, - E. (1) K, C 2H 5; (2) HA, heat; (3) H 3O +, H 2O, heat Br 33. trans-3-methylcyclopentanol is treated with SO 2Cl in the presence of base. The product of this reaction is then heated with KI in methanol. What is the final product? A. trans-1-iodo-3-methylcyclopentane B. cis-1-iodo-3-methylcyclopentane C. 1-Methylcyclopentene D. 2-Methylcyclopentene E. 3-Methylcyclopentene 34. Select the structure of the major product formed from the following reaction. A. I B. II C. III D. IV E. V 1. Hg(OOC ) 2 THF, H 2 O 2. NaBH 4, Na? CH 2 HO I II III IV V 6

7 35. Oxymercuration-demercuration of 3-methylcyclopentene produces this/these product(s): A. I B. II C. III D. IV E. Both III and IV HO CH 2 I II III IV EXTRA CREDIT 36. The tertiary alcohol below was reacted with PCC in CH 2Cl 2 and gave a product, C 12H 12O. The product had a strong absorption in the IR spectrum at 1700 cm -1. Predict which of the following is the product. (Note: PCC is pyridinium chlorochromate, [C 5H 5NH + ][ClCrO 3 ].) 37. (2R,3S )-3-Bromo-2-methyl-1-butanol is the IUPAC name for which of the following alcohols? NAME DATE ANSWER SHEET CHE 325 CHAP 15 ASSIGN SS II

Chemistry 262 Homework 2 Part II Winter 2018

Chemistry 262 Homework 2 Part II Winter 2018 The following homework covers Chapter 10 in Loudon & Parise s Organic Chemistry, 6 th ed. and contains 24 questions, valued at 0.3333 point each, as well as