CHE 275 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- 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- B. 3-hexyne C. 2-heptyne D. 3-heptyne

4. Predict the major product(s) in the reactions below. A. 1- 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- 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.

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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) , NaNH2 B. (1) , NaNH2 (2) 1-bromobutane (2) 1-bromopentane 2+ 2+ (3) H2O, Hg , H2SO4 (3) H2O, Hg , H2SO4

C. (1) hexyne, NaNH2 D. (1) 1-, 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.

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17. Ozonolysis of an 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° CCC 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)

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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)CH2CCC(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- 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 HCC 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.

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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

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