HEM 241 ALKYNES HAP 9 ASSIGN 1. What is the IUPA name of the following compound A. 5-propyl-3-heptyne B. 5-isopropyl-3-heptyne. 5-ethyl-3-octyne D. 4-ethyl-5-octyne 2. What is the correct IUPA name for the following molecule A. (Z )-3-Methyl-3-penten-1-yn-5-ol B. (E )-3-Methyl-3-penten-1-yn-5-ol. (E )-3-Methyl-2-penten-4-yn-1-ol D. (Z )-3-Methyl-2-penten-4-yn-1-ol E. (E )-4-Hydroxymethyl-3-methyl-3-penten-1-yne 3. Which of the following gives only one organic product on ozonolysis A. 2-hexyne B. 3-hexyne. 2-heptyne D. 3-heptyne 4. Predict the major product(s) in the reactions below. A. 1-nonyne B. 2-nonyne. cis-2-nonene D. trans-2-nonene 5. Which one of the following alkynes gives a single ketone in the acid-catalyzed hydration of each A. 2-decyne B. 3-decyne. 4-decyne D. 5-decyne 6. Which sequence of reactions works best in synthesizing cis-3-nonene 7. Which sequence of reactions below works best in carrying out the following conversion A. (1) HBr (2) excess NaNH 2 B. (1) Br 2 (2) excess NaNH 2. (1) Br 2, H 2 (2) excess NaNH 2 D. (1) H 2, H 2S 4(cat.) (2) excess NaNH 2 8. Which of the following is the correct IUPA name of the product for the reaction shown below A. cis-2-methyl-5-heptene B. trans-2-methyl-5-heptene. cis-6-methyl-2-heptene D. trans-6-methyl-2-heptene 9. When alkynes are treated with sodium metal, Na, in liquid ammonia, sodium acts as a A. Brønsted acid. B. Brønsted base.. reducing agent. D. catalyst. 1 P a g e
10. What is the product of the following reaction sequence A. 1-hexanol B. 2-hexanol. 1,2-hexanediol D. 1-hexene 11. What is the greatest number of atoms that you would expect to be co-linear in the molecule shown below A. five B. six. seven D. eight E. nine 12. What reagents are required to effect the following conversion A. Mg, ether B. H 3H 2- Na+. NaNH 2 (1 equiv.) D. NaNH 2 (2 equiv.) E. NaNH 2 (3 equiv.) 13. Select the best reaction sequence to make the following ketone. A. (1) propyne, NaNH 2 B. (1) acetylene, NaNH 2 (2) 1-bromobutane (2) 1-bromopentane (3) H 2, Hg 2+, H 2S 4 (3) H 2, Hg 2+, H 2S 4. (1) hexyne, NaNH 2 D. (1) 1-pentyne, NaNH 2 (2) bromomethane (2) bromoethane (3) H 2, Hg 2+, H 2S 4 (3) H 2, Hg 2+, H 2S 4 14. How would you carry out the following conversion A. (1) H 2/Lindlar Pd (2) HBr B. (1) H 2/Lindlar Pd (2) HBr, peroxides. (1) HBr (1 eq) (2) H 2/Pd D. (1) Br 2 (1eq) (2) H 2/Pd 15. What is the major product of the reaction shown below A. 1,1-dichlorobutane B. 1,2-dichlorobutane. 2,2-dichlorobutane D. 1,12,2-tetrachlorobutane 16. Why can't methanol, H 3H, be used as a solvent for sodium amide, NaNH 2 A. Sodium amide is nonpolar and methanol is polar. B. Sodium amide is polar and methanol is nonpolar.. Sodium amide does an acid-base reaction with methanol. D. There would be no ion-dipole attractive forces between the two compounds. 2 P a g e
17. zonolysis of an alkyne gave the two compounds shown below. What is the IUPA name of the original alkyne A. 2,2-dimethyl-3-octyne B. 3,3-dimethyl-4-octyne. 2,2-dimethyl-3-heptyne D. 6,6-dimethyl-3-heptyne H 3H 2H 2 2H and (H 3) 3 2H 18. Which of the following ketones cannot be made by the acid-catalyzed hydration of an alkyne 19. Predict the product of the following reaction. A. 1-bromo-1-chlorocyclopentane. 1-bromocyclopentene B. 1-bromo-2-chlorocyclopentane D. cyclopentene 20. What is the only correct statement about cyclohexyne A. It is acidic. B. It has four 109 bond angles.. It is planar. D. It is too strained to be synthesized. 21. How many organic products do you expect from this reaction A. one B. two. three D. four H 3 H 2 cat. H 2 S 4 cat. HgS 4 22. What major product results from this reaction A B 3 H 2 2 H 2 H D 23. The product of this reaction would be A. only (S) B. only (R). (R) + (S) D. achiral H H 3 H H 2 Pt only (S) 3 P a g e
24. The product of this reaction would be A. only (S) B. only (R). (R) + (S) D. achiral 25. How many carbons lie in a straight line in 2-methyl-3-hexyne A. 2 B. 3. 4 D. 6 26. The name of the following compound is: H 3H(H 2H 3)H 2 (H 3) 3 A. 6-ethyl-2,2-dimethyl-3-heptyne B. 2,2,6-trimethyl-3-octyne. tert-butylisopropylacetylene D. 2,6-dimethyl-3-heptyne 27. The sequence of steps needed for the conversion of 1-butene to 1-butyne is A. HBr/peroxides; then alcoholic KH B. Hl/no peroxides: then NaNH 2/liquid NH 3. Br 2/l 4; then NaNH 2/liquid NH 3 D. KMn 4 cold; then H 2S 4/heat 28. Which is the correct order of decreasing basicity in the anions (most basic to least basic) H NH 2 H H 3H 2 H 2=H A B D E A. A > B > > D > E B. D > E > B > > A. > B > D > A > E D. D > E > > B > A 29. Which reagent can distinguish between 1-hexyne and 1-hexene A. KMn 4 B. H 2S 4. Br 2/l 4 D. AgN 3/NH 4H 30. The sequence of reagents needed for the conversion of 1-bromopropane to propyne is A. alcoholic KH/heat; then Br 2/l 4; then NaNH 2/NH 3 B. (H 3) 3 - K + /heat; then HBr; then NaNH 2/NH 3. alcoholic KH/heat; then Br 2 /l 4; then H 2S 4 D. alcoholic KH, then H 2/Pt; then NaNH 2/NH 3 31. Predict the major product of the following reaction. 4 P a g e
32. Identify compound Y. A. 2-bromobutane B. meso-2,3-dibromobutane. racemic (2R,3R) and (2S,3S)-2,3-dibromobutane D. 2,3-dibromo-2-butene NAME DATE ANSWER SHEET HEM 241 HAP 9 ASSIGN 1. 11. 21. 31. 2. 12. 22. 32. 3. 13. 23. 33. 4. 14. 24. 34. 5. 15. 25. 35. 6. 16. 26. 36. 7. 17. 27. 37. 8. 18. 28. 38. 9. 19. 29. 39. 10. 20. 30. 40. FALL 2018 5 P a g e