Final Examination, Organic Chemistry 1 (CHEM 2210) December 2000 Version *A* A. B. C. D.

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1 Final Examination, rganic hemistry 1 (EM 2210) December 2000 Version *A* 1. What are the hybridization of, and the geometrical shape around, the nitrogen atom in the following molecule? N 3 3 A. sp, linear B. sp, bent. sp2, trigonal planar D. sp2, bent 2. Which of the following compounds is a cis isomer? A. B.. D. 3. The nitrogen atom in which of the following molecules/ions has the largest (positive) formal charge?.... A. 3 N 3 B. 3 N 3... (3)4N D. 3 N: 3 4. Which of the following compounds is NT a structural isomer of cyclohexanol? A. B.. D. 5. What class of compounds does the following structure belong to? A. Ketone B. Ether. Ester D. Aldehyde

2 6. ow many sigma bonds are present in the following molecule? A. 11 B D What is the direction of the dipole moment in the molecule whose structure is shown below? 3 3 N A. B.. D. 8. Which of the following functional groups is NT present in the following molecule? A. 2 alcohol B. Alkene. Ester D. Ether 9. What is the name of the following compound? A. 1-ethyl-8-methylbicyclo[4.3.0]nonane B. 1-ethyl-3-methylbicyclo[4.3.0]nonane. 5-ethyl-3-methylbicyclo[4.3.0]nonane D. 3-ethyl-1-methylbicyclo[4.3.0]nonane

3 10. Which of the following is an alkylacetylene? A. B.. D. 11. What is the IUPA name of the compound shown? A. 2-methyl-4-ethylheptane B. 4-ethyl-2-methylheptane. 4-ethyl-6-methylheptane D. 2-methyl-4-propylhexane 12. The most stable chair conformation of trans-4-tert-butylcyclohexanol has: A. the group equatorial and the tert-butyl group equatorial. B. the group axial and the tert-butyl group axial.. the group equatorial and the tert-butyl group axial. D. the group axial and the tert-butyl group equatorial. 13. What would you use to carry out the following transformation? A. 2, light B. NaN 2, N 3. Zn, l D. 2, Pd 14. What is the IUPA name of the compound shown? A. trans-1-isopropyl-2-cyclohexanol B. cis-2-isopropylcyclohexanol. trans-2-isopropylcyclohexanol D. cis-2-sec-butylcyclohexanol

4 15. Which of the following shows 1-bromo-2-iodoethane in its most stable conformation? I I A. B. I. D. I 16. What is the name of the following compound? 2 3 A. cis-3-bromo-1-buten-3-ol B. (S)-2-bromo-3-buten-2-ol. (R)-2-bromo-3-buten-2-ol D. cis-(r)-2-bromo-3-buten-2-ol 17. ow many stereoisomers does the given compound have? 3 A. 2 B D. 16

5 18. Which of the following is true about the following reaction? 2 l 3 Zn, l 3 A. The product will have R configuration. B. A meso compound is produced.. The product will have S configuration. D. The product is not optically active. 19. onsider the structure shown N Ephedrin, I 3 Which of these Fischer projection formulas corresponds to I? A. 6 5 B N 3 N D N 3 3 N 3

6 20. Which of the following statements is true of (2R,3S)-2,3-difluorobutane? A. It has 3 stereoisomers: one enantiomer and 2 diastereomers. B. It has 2 stereoisomers and both are diastereomers of it.. It has one stereoisomer which is an enantiomer of it. D. It is a meso compound and, therefore, has no stereoisomers. 21. What is the mechanism of the following reaction? + 2 A. S N 1 B. S N 2. E1 D. E2 22. Which of the following is optically inactive? A. B.. D. 23. onsider the following reaction water ethanol 3 () 3 + Which of the following changes below INREASES the rates of BT the S N 1 and S N 2 reactions? A. Use 3 I 3 instead of 3 3 B. Use 3 2 instead of 3 3. Decrease the concentration of 3 3 D. Increase the concentration of hydroxide ion

7 24. Which of the following alkenes is a Z diastereomer? A. B.. D. 25. Which of these alkenes has the GREATEST heat of hydrogenation? A. B.. D. 26. Which of the following reagents will complete the reaction shown? l? + A. K B. 2 S 4. Ni 2 B D. NaN The index of hydrogen deficiency of is... A. 20 B D The alkene that is the major product of the following dehydration reaction is: P 4 heat A. disubstituted, cis B. disubstituted, trans. trisubstituted D. tetrasubstituted

8 29. What is the correct name for the following compound? l A. (Z)-2-chloro-4-methyl-2-pentene B. (E)-2-chloro-4-methyl-2-pentene. (Z)-4-chloro-2-methyl-3-pentene D. (E)-4-chloro-2-methyl-3-pentene 30. Dehydrohalogenation reactions usually give the most stable alkene as their major product when more than one product is possible. An exception to this rule occurs when which of the following reagents is employed as the base? A. potassium tert-butoxide B. sodium amide. potassium hydroxide D. nickel boride 31. Which of the following alcohols will dehydrate most rapidly with sulfuric acid and heat? A. B.. D. 32. What is the major organic product of the following reaction? 3 2 mol A B D

9 33. What reagents would you use to carry out the following reaction? A. KMn 4, -, heat B. KMn 4 (cold, dilute) , then 2 / 3 + D. 3, then Zn/ Which of the following reactions has a mechanism that involves the formation of a cyclic intermediate from acyclic starting materials? A. dehydration of an alcohol B. addition of to an alkene. chlorination of an alkane D. addition of bromine to an alkene 35. What is the major organic product of the following reaction? ( 3 ) l? A. ( 3 ) 2-3 l B. ( 3 ) l 3. ( 3) l D l

10 36. What is the major organic product of the following reaction? A. B.. D. 37. What is the major organic product of the reaction shown? no peroxides? A B. 3 2 ()= () 3 D () Which of these reagents ANNT be used to distinguish between cyclohexane and cyclohexene? A. 2 /l 4 B. conc. 2 S 4. KMn 4 D. Na 39. What is the major organic product of the reaction shown? 3 B3 TF 22, > > A. B.. D.

11 40. Which of these is the best way to synthesize the ether shown? 3 A. + 3 B I. I D. + 3 I 41. Which of the following acid-base reactions does not occur? _ A. B. _ 3 2 _. _ D N When is oxymercuration-demercuration the preferred method for the synthesis of an alcohol from an alkene? A. When the chemist wants the anti-markovnikov product. B. When the chemist wants a Markovnikov product with carbocation rearrangements.. When the chemist wants an anti-markovnikov product with no rearrangement. D. When the chemist wants a Markovnikov product with no rearrangements.

12 43. What is the IUPA name of the compound shown? l A. 1-hydroxy-2,2-dimethyl-3-chlorocyclohexane B. 4-hydroxy-2,2-dimethylcyclohexyl chloride. 4-chloro-2,2-dimethylcyclohexanol D. 4-chloro-2,2-dimethylcyclohexyl alcohol 44. Which of the following is the least soluble in water? A. 3 B D What is the major organic product of the following reaction? ( 3 ) 3 + conc. 3 A. B. ( 2 3 ) 3 3. ( 3 ) 2 2 D. ( 3 ) Which of the following radicals is the most stable?. A. B.. D....

13 47. Which of the following is an initiation step? A B. heat D Which of the following reactions has an E act = 0? A. + 2 light B D ow many hydrogen atoms are there in the compound shown? l A. 13 B D The reaction of 1-butene with in the presence of peroxides yields 1-bromobutane. The mechanism for the reaction involves: A. attack on the alkene by a bromine atom,.. B. attack on the alkene by a hydrogen atom,... attack on the alkene by a + ion. D. attack on the alkene by a + ion.

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