CHEMISTRY FINAL EXAM June 25, 2005
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1 CEMISTRY FINAL EXAM June 25, 2005 Name... The total number of points is 100. The total exam time is 120 min (2 h). Good luck! PART I: CNCEPTS 1. (10 pts) Mark as true (T) or false (F) the following statements. Do not explain! The resonance structures of a particular compound are always in a state of rapid equilibrium; Transition states are usually the local minima on the potential energy diagrams; The eclipsed conformation of ethane is a local minimum; Free-radical halogenation occurs with formation of electron-deficient species; Polar hydrohalogenation obeys the Markovnikov rule; Dehydrohalogenation obeys the Zaitsev rule; Diastereomers are non-superimposable mirror images; Both S N 2 and E2 reactions are accelerated by increase of temperature; Antiaromatic compounds are non-planar; Nonaromatic compounds are always acyclic; PART II: CIRCLE ALL TAT APPLY 2. Circle all that apply: A. (3 pts) The ammond Postulate states that: a. Related species with similar charges have similar structures; b. Related species with similar energies have similar structures; c. Related species with similar structures have similar dipole moments; B. (3 pts) E2 reactions: a. ccur with inversion of configuration; b. Require strong bases; c. bey the Zaitsev rule; d. Are subject to stereoelectronic requirements; C. (3 pts) Meso-compounds: a. Are optically active; b. Do not contain chiral centers; c. Contain one chiral center; d. ave non-superimposable mirror images; D. (3 pts) Aromatic compounds: a. Are all compounds with (4n+2) π-electrons; b. Are always cyclic; c. Are destabilized compared to their acyclic analogs; d. ave lower reactivity; PART III: MULTIPLE CICE 3. (3 pts) Circle the most stable alkene: A. 2-methyl-2-hexene B. 2-methyl-1-hexene C. (E)-3,4-dimethyl-3-hexene D. trans-cyclopentene E. propene 4. (3 pts) Circle the most acidic of the following compounds: A. Potassium hydride (K) B. 2-methylphenol C. Cyclopentanol D. enylacetylene E. Ammonia
2 5. (2 pts) Circle the most stable radical. Do not explain! 6. (2 pts) Circle the most stable carbocation. Do not explain! 7. (3 pts) Circle the enantiomer of (2R, 3S)-2-bromo -3-phenylbutane. C 3 C 3 C 3 C 3 C 3 C 3 C 3 C 3 3 C C 3 8. (2 pts) Circle the product of conjugate addition of to 2,5-dimethyl-2,4-hexadiene. 9. (3 pts) Circle the product of hydroboration-oxidation of 1-methylcyclopentene. C 3 C 3 C 3 C (2 pts) Circle the product of epoxidation of (E)-2-pentene. 11. (3 pts) Circle the product of reaction of cis-2-butene with 2 / 2. 3 C C 3 3 C C 3 3 C C 3 3 C C 3 3 C C (2pts) Circle the product of Birch reduction of toluene.
3 13. (2 pts) Circle the most reactive substrate in S N 2 reactions. I PART IV: NMENCLATURE 14. (5 pts) Draw the structure of each of the following compounds. 2,6-difluoroaniline 2-ethyl-4-methylphenol imidazole m-chlorobenzoic acid benzyl iodide PART V: TERY AND MECANISMS 15. (3 pts) Label each of the structures below as aromatic, antiaromatic or non-aromatic. Do not explain! N N N N N N S N 16. (4 pts) The addition of to 1-methoxycyclohexene occurs with the formation of a single regioisomer. ffer a structural rationalization for this phenomenon and suggest a detailed mechanism (structures and equations please!) of the above reaction. C 3 + C 3 PART VI: REACTINS 17. (28 pts) Predict the principal organic product(s) of each of the following reactions.
4 NBS heat light + NC CN heat C 3 K C(C 3 ) 3 t-butanol (C 3 ) 2 S C 3 KMn 4 water/ t-butanol 2 C S 4 gs 4 Ts NaN 3 DMF 3 C Na Na C 3 liq. N 3 C 2 5 liq. N MCPBA C (3 pts) ow would you use the Diels-Alder reaction to prepare the following products? Show the starting diene and dienophile in each case (With precise stereochemistry!!). C 3 C 2 C 3 A. C 3 CC 3 C 3 CC 3 B. CN PART VII: SYNTESIS 19. Propose a plausible step-by-step synthetic sequence for each of the following transformations (More than one step is required! Be very specific!). Start from the indicated compound and use any other necessary organic or inorganic reagents.
5 A. (4 pts) acetylene??? B. (4 pts) 20. (3 pts) BNUS PRBLEM (In order to receive credit for this problem, it has to be solved entirely!!). Shown below are some cyclic ketones. Cyclopropenone and cycloheptatrienone are very stable compounds, while cyclopentadienone is extremely unstable. ffer a structural rationalization to account for these facts (More structures, fewer words please!). cyclopropenone cyclopentadienone cycloheptatrienone
3. (6 pts) Provide an acceptable name for each of the following molecules: OH
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H C C C C H C H C C H OH. Cl H CH 3. Br CH 3. H Br H OH H 3 C. CHEMISTRY MIDTERM # 3 June 17, Name...
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H C C C C H C H C C H H. Cl H CH 3 O. Br CH 3 OH H 3 C. H Br H
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