CHE 275 ALKYNES CHAP 9 ASSIGN 1. What is the IUPAC name of the following compound? A. 5-propyl-3-heptyne B. 5-isopropyl-3-heptyne C. 5-ethyl-3-octyne D. 4-ethyl-5-octyne 2. What is the correct IUPAC 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 C. (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 C. 2-heptyne D. 3-heptyne 4. Predict the major product(s) in the reactions below. A. 1-nonyne B. 2-nonyne C. 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 C. 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 NaNH2 B. (1) Br2 (2) excess NaNH2 C. (1) Br2, H2O (2) excess NaNH2 D. (1) H2O, H2SO4(cat.) (2) excess NaNH2 8. Which of the following is the correct IUPAC name of the product for the reaction shown below? A. cis-2-methyl-5-heptene B. trans-2-methyl-5-heptene C. 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. C. 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 C. 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 C. seven D. eight E. nine 12. What reagents are required to effect the following conversion? A. Mg, ether B. CH3CH2O- Na+ C. NaNH2 (1 equiv.) D. NaNH2 (2 equiv.) E. NaNH2 (3 equiv.) 13. Select the best reaction sequence to make the following ketone. A. (1) propyne, NaNH2 B. (1) acetylene, NaNH2 (2) 1-bromobutane (2) 1-bromopentane 2+ 2+ (3) H2O, Hg , H2SO4 (3) H2O, Hg , H2SO4 C. (1) hexyne, NaNH2 D. (1) 1-pentyne, NaNH2 (2) bromomethane (2) bromoethane 2+ 2+ (3) H2O, Hg , H2SO4 (3) H2O, Hg , H2SO4 14. How would you carry out the following conversion? A. (1) H2/Lindlar Pd (2) HBr B. (1) H2/Lindlar Pd (2) HBr, peroxides C. (1) HBr (1 eq) (2) H2/Pd D. (1) Br2 (1eq) (2) H2/Pd 15. What is the major product of the reaction shown below? A. 1,1-dichlorobutane B. 1,2-dichlorobutane C. 2,2-dichlorobutane D. 1,12,2-tetrachlorobutane 16. Why can't methanol, CH3OH, be used as a solvent for sodium amide, NaNH2? A. Sodium amide is nonpolar and methanol is polar. B. Sodium amide is polar and methanol is nonpolar. C. 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. Ozonolysis of an alkyne gave the two compounds shown below. What is the IUPAC name of the original alkyne? A. 2,2-dimethyl-3-octyne CH3CH2CH2CO2H and (CH3)3CCO2H B. 3,3-dimethyl-4-octyne C. 2,2-dimethyl-3-heptyne D. 6,6-dimethyl-3-heptyne 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 C. 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° CCC bond angles. C. 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 H2O CH3 ? C. three cat. H SO D. four 2 4 cat. HgSO4 22. What major product results from this reaction? O O O3 ? A B H2O CO H 2 O CO2H C D 23. The product of this reaction would be A. only (S) H B. only (R) C C. (R) + (S) C D. achiral H2 ? H Pt CH3 only (S) 3 | P a g e 24. The product of this reaction would be A. only (S) B. only (R) C. (R) + (S) D. achiral 25. How many carbons lie in a straight line in 2-methyl-3-hexyne? A. 2 B. 3 C. 4 D. 6 26. The name of the following compound is: CH3CH(CH2CH3)CH2CCC(CH3)3 A. 6-ethyl-2,2-dimethyl-3-heptyne B. 2,2,6-trimethyl-3-octyne C. 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 KOH B. HCl/no peroxides: then NaNH2/liquid NH3 C. Br2/CCl4; then NaNH2/liquid NH3 D. KMnO4 cold; then H2SO4/heat 28. Which is the correct order of decreasing basicity in the anions (most basic to least basic) HO NH2 HCC CH3CH2 CH2=CH A B C D E A. A > B > C > D > E B. D > E > B > C > A C. C > B > D > A > E D. D > E > C > B > A 29. Which reagent can distinguish between 1-hexyne and 1-hexene? A. KMnO4 B. H2SO4 C. Br2/CCl4 D. AgNO3/NH4OH 30. The sequence of reagents needed for the conversion of 1-bromopropane to propyne is A. alcoholic KOH/heat; then Br2/CCl4; then NaNH2/NH3 - + B. (CH3)3CO K /heat; then HBr; then NaNH2/NH3 C. alcoholic KOH/heat; then Br2/CCl4; then H2SO4 D. alcoholic KOH, then H2/Pt; then NaNH2/NH3 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 C. racemic (2R,3R) and (2S,3S)-2,3-dibromobutane D. 2,3-dibromo-2-butene NAME_______________________________________ DATE______________ ANSWER SHEET CHEM 241 – CHAP 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 2019 5 | P a g e .