C201HS06T1

C201HS06T1 - COM 11. ED4 - PR EM P COM CHM 201N- Organic...

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Unformatted text preview: COM 11. ED4 - PR EM P COM CHM 201N- Organic Chemistry I Feb 16, 2006 - PR EM ED4 11. Exam 1 COM Name (Please Print):____KEY____ - PR EM ED4 11. ANSWERS ON LAST PAGE ED4 11. COM You have: → Test Form 1 ← COM - PR EM To be properly graded, you must indicate your correct Test Form number on your Scantron!! - PR EM ED4 11. Test taking strategy: Questions are in no particular order of difficulty. Answer questions you are more comfortable with first. Flag the harder ones and return to them later. 11. COM 31 questions, 100 pts total. All questions worth an equal amount: ~3¼ pts/question. MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 The last page is a scratch page and on the back contains a periodic table and a table of bond dissociation energies. You can rip it out!! PRE MED 411 .CO MPRE MED 411 .CO O 1 O OM - PR EME D41 1.C OM P 1.C OM - PR EME D41 1.C 1. Which formula represents a compound that is different from all the others? c - PR EME D41 1.C OM - PR EME D41 b a e 11. COM d - PR EM ED4 11. COM - PR EME D4 11. COM - PR EME D4 2. What is the simplest alkane, i.e., the one with the smallest molecular weight, which possesses primary, secondary and tertiary carbon atoms? A) 2-methylpropane B) 2-methylbutane C) 2-methylpentane D) 3-methylpentane E) 2,2-dimethylbutane - PR EM ED4 11. COM - PR EM 2-ethyl-4,5-dimethylhexane 5-ethyl-2,3-dimethylhexane 5-ethyl-2,3-dimethylhexane 3,5,6-trimethylheptane 2,3,5-trimethylheptane PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM A) B) C) D) E) ED4 11. COM - PR EM ED4 11. COM 3. The IUPAC name for the following compound is: 2 - PR EME D41 1.C OM P H H H H3C H3 C H H - PR EME H H3C CH3 H H CH3 H H C H3 H H CH3 A D41 HH - PR EME H H H 3C H 1.C OM H3 C D41 1.C OM 4. Rank the following conformers of butane in order of decreasing stability (in other words, from most stable to least) H CH3 C D H CH 3 E 11. COM - PR EME E > (B = F) > (D = A) > C D > (C = A) > (B = E) > F F>B>E>C>A>D F > (B = E) > (C = A) > D B>E>F>D>C>A - PR EME D4 a. b. c. d. e. D41 1.C OM B H H HH - PR EME D4 11. COM 5. The least stable conformation of butane experiences which type(s) of strain: torsional only torsional and steric torsional and angle steric and angle torsional, steric, and angle COM - PR EM ED4 11. COM a. b. c. d. e. ED4 11. COM - PR EM ED4 11. 6. For the equilibrium PRE MED - PR EM COM 11. ED4 - PR EM 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM A) B) C) D) E) the two substances which both are acids are: H2O and H3O+ CH3NH3+ and H2O CH3NH3+ and CH3NH2 CH3NH3+ and H3O+ CH3NH2 and H2O 3 H CH3 F OM 1.C D41 - PR EME 1.C OM - PR EME D41 1.C OM Which of the following is not a Lewis base? NH3 HBF3 H2O H3C- PR EME D41 7. A) B) C) D) E) P ED4 11. COM - PR EME D4 I II III IV V COM - PR EM A) B) C) D) E) 11. COM - PR EME D4 11. COM - PR EME D41 1.C OM 8. Which compound would have the lowest boiling point? (assume all have approximately the same molecular weight) 11. COM - PR EM ED4 11. 9. Which is predicted to have the highest boiling point? A) CH3CH2CH2CH3 B) COM - PR EM ED4 C) CH3CH2CH2CH2CH3 D) PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. E) 4 - PR EME D41 1.C OM P 1.C OM 10. The early oral contraceptive, Enovid, contains how many sp3 carbons? D41 OH C CH OM 1.C D41 Enovid O D41 1.C OM 11. Of those sp3 carbons, how many are tertiary? 11. COM - PR EME 1 2 3 4 5 CH 3 - PR EME D4 a. b. c. d. e. CH 3 - PR EME 1 3 14 15 20 - PR EME a. b. c. d. e. C CH - PR EME D4 11. COM 12. Enovid contains how many sp2 carbons? a. 1 b. 2 c. 3 d. 4 e. 5 OH COM Enovid - PR EM ED4 11. O - PR EM ED4 11. COM - PR EM ED4 11. COM 13. Which structure does not have molecular formula C8H12? b e d c - PR EM ED4 11. COM a - PR EM ED4 11. the same compound different compounds that are constitutional isomers different compounds that are geometric isomers different compounds that are not isomers PRE MED 411 .CO MPRE M ED4 11. COM a. b. c. d. COM 14. The pair of structures at right, represent: 5 and - PR EME D41 1.C OM P 1.C OM - PR EME D41 1.C 3-hydroxymethylheptane 3-hydroxymethylhexane 3-methyloxyheptane 2-ethyl-1-hexanol 2-ethyl-1-heptanol - PR EME D41 A) B) C) D) E) OM - PR EME D41 1.C OM 15. What is the correct IUPAC name for the following compound? 3-hexene 1,3-dimethylcyclohexane 3,4-dimethyl-3-hexene 2,3,4-trimethyl-2-hexene None of the above - PR EME D4 11. COM - PR EME D4 a. b. c. d. e. 11. COM 16. Which of the following can not exist as cis/trans isomers Br ED4 11. COM 17. The IUPAC name of the compound at right is: (E) 1- isopropyl-1-isobutyl-2,3-dibromo-1-propene (Z)-1,2-dibromo-3-isopropyl-5-methyl-2-hexene (E)-1,2-dibromo-3-isopropyl-5-methyl-2-hexene (Z)-1,2-dibromo-3-isobutyl-4-methyl-2-pentene (E)-1,2-dibromo-3-isobutyl-4-methyl-2-pentene Br 11. COM - PR EM ED4 11. COM - PR EM a. b. c. d. e. b a c d e PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 18. Which conformation represents the most stable conformation of cis-1-tert-butyl-4methylcyclohexane? 6 OM 1.C D41 - PR EME P - PR EME OM 1.C D41 I II III More than one of the above None of the above - PR EME A) B) C) D) E) D41 1.C OM - PR EME D41 1.C OM 19. When properly labeled, which compound should contain a nitrogen atom with a formal positive charge? COM . COM - PR EME D4 11. COM - PR EME D4 11. 20. The most stable conformation of trans-1-tert-butyl-3-methylcyclohexane is the one in which: A) the tert-butyl group is axial and the methyl group is equatorial. B) the methyl group is axial and the tert-butyl group is equatorial. C) both groups are axial. D) both groups are equatorial. E) the twist boat conformation is adopted. 11. COM - PR EM ED4 11. COM - PR EM ED4 11. 21. According to molecular orbital theory, the σ and π bonds that comprise a carbon-carbon double bond are formed by overlap of ___________ atomic orbitals, respectively. A) two sp2 and two p B) two p and two sp2 C) one s and two p D) two s and two p E) none of the above - PR EM ED4 11. COM - PR EM ED4 22. Which molecule would you expect to have no dipole moment (i.e., µ = 0 D)? A) CHF3 B) COM - PR EM ED4 11. COM C) :NF3 D) PRE MED 411 .CO MPRE M ED4 11. E) CH2F2 7 OM 1.C D41 - PR EME - PR EME D41 1.C OM 23. Which compound would you expect to have the lowest boiling point? (assume all have approximately the same molecular weight) A) - PR EME D41 1.C OM B) 1.C OM C) 11. COM - PR EME D41 D) 11. COM - PR EME D4 E) - PR EM ED4 11. COM - PR EME D4 24. Which of these compounds is a secondary alkyl chloride? A) CH3CH2CH2CH2CH2Cl B) ED4 11. COM C) COM - PR EM D) ED4 11. COM - PR EM ED4 Which of the acids below would have the strongest conjugate base? CH3CH2OH pKa = 18 CH3CO2H pKa = 4.75 ClCH2CO2H pKa = 2.81 Cl2CHCO2H pKa = 1.29 Cl3CCO2H pKa = 0.66 PRE MED 411 .CO MPRE M ED4 11. COM - PR EM 25. A) B) C) D) E) 11. COM - PR EM ED4 11. E) Two of these 8 P - PR EME D41 1.C OM P - PR EME D41 1.C OM 26. In the reaction of 2-butene with HBr, the step that sets the overall rate for the reaction is best represented by: H b Br Br - Br d Br - - PR EME D41 H 1.C c OM - PR EME D41 1.C OM a H Br b Br - PR EME D4 11. COM a - PR EME D4 11. COM 27. In the reaction of 2-butene with HBr, the step with a negative ∆G° is best represented by: H Br d Br - PR EM ED4 11. COM c 11. COM - PR EM ED4 11. (E)-1-bromo-1-chloro-2-methyl-1-hexene (Z)-1-bromo-1-chloro-2-methyl-1-hexene (E)-2-bromochloromethylenehexane (Z)-2-bromochloromethylenehexane None of the above PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 A) B) C) D) E) COM - PR EM ED4 11. COM 28. Which is a correct name for the following compound? 9 - - - PR EME D41 1.C OM P - PR EME D4 11. COM I II III IV V 11. COM A) B) C) D) E) - PR EME D41 1.C OM - PR EME D41 1.C OM - PR EME D41 1.C OM 29. Which compound is a primary amine with the formula C5H13N? ED4 11. COM - PR EM ED4 11. COM - PR EME D4 30. The number of unique monochloro (“containing one chlorine”) derivatives of propene is: (i.e., how many acyclic (non-cyclic) compounds with molecular formula C3H5Cl exist?) A) 2 B) 3 C) 4 D) 5 E) 6 + H - Cl Cl COM - PR EM ED4 11. COM - PR EM 31. (To answer this question, you’ll need to refer to the table of bond dissociation energies on the back page. Assume it takes 63 kcal/mol to break the π bond of propene.). - PR EM ED4 11. The above reaction is: PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM a. exothermic by greater than 10 kcal/mol b. exothermic by less than 10 kcal/mol c. endothermic by greater than 10 kcal/mol 1. endothermic by less than 10 kcal/mol 10 M .CO 411 .CO MPRE MED P PRE MED 411 .CO MPRE ME D41 1.C OM - PR E MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 .CO MPRE MED 411 1. d 2. b 3. e 4. d 5. b 6. d 7. c 8. a 9. c 10. d 11. d 12. c 13. e 14. c 15. d 16. d 17. b 18. b 19. d 20. b 21. a 22. b 23. c 24. e 25. a 26. c 27. d 28. a 29. c 30. c 31. a 11 ...
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