GOOD SAMARITAN COLLEGES Cabanatuan City College of Allied Health Professions Name: ___________________________________ Instructor: ________________________________ Course/Year: _____________________________ Permit No: ________________________________ Preliminary Examination Chem 3 – Organic Chemistry DIRECTION: Choose the letter of your answer from the choices given. Shade the letter corresponding to your answer on the provided answer sheet. 1. Theory that says “the intervension of vital force is necessary for the synthesis of organic compounds.” a. Structural theory b. Vitalism c. Fundamental Theory d. Resonance Theory 2. Based on Structural theory, Oxygen is a. monovalent c. trivalent b. divalent d. tetravalent 3. Structure representation where a molecule is represented by two or more Lewis structure that differ only in the position of electrons. a. Resonance b. Structural Isomers c. Enantiomer d. Functional Group 4. Compounds that have the same molecular formula but differ in their connectivity. a. Resonance b. Structural Isomers c. Enantiomer d. Functional Group 5. Structural representation that shows only carbon skeleton. a. Dash Formula b. Dot Formula c. Condensed Formula d. Bond Line Formula 6. An geometric isomer of cis-2-butene a. cis-1-butene c. cyclobutene b. trans-2-butene d. 2-methyl propene 7. Functional group common to carboxylic acid and ester. a. carbonyl b. carboxyl c. hydroxyl d. oxygen For #8-11, consider the hydrocarbon 2,2-dimethylbutane 8. How many tertiary Hydrogen is present a. 0 b. 1 c. 2 d. 3 9. How many tertiary Carbon is present a. 0 b. 1 c. 2 d. 3 10. How many Secondary Hydrogen is present a. 0 b. 1 c. 2 d. 3 11. How many secondary Carbon is present a. 0 b. 1 c. 2 d. 3 12. 2- methyl-2-propanol is a a. primary alcohol b. secondary alcohol c. tertiary alcohol d. NOTA 13. Which of the following compounds has the highest boiling point. a. Propanol b. Butanol c. Pentanol d. Hexanol 14. Hydrocarbon family with the general formula CnH2n+2 with no rings a. Alkanes b. Alkenes c. Alkynes d. Alcohol 1| 15. A carboxylic acid derivative with an N atom replacing the hydroxyl group. a. amine b. amide c. ester d. ether 16. The IUPAC name of CH3CH2CH(CH3)CH(CH2CH2CH3)CH(CH3)CH(CH3)CH3 a. 2,3,5-trimethyl-4-propyl-heptane b. 4-sec-butyl-2,3-dimethylheptane c. 4-tert-butyl-2,3-dimethylheptane d. 4-butyl-2,3-dimethylheptane 17. Which of the following hydrocarbons is most soluble in water? a. methanol b. propanol c. butanol d. decane 18. Which is not an isomer of C3H6 a. propene c. cyclopropane b. 2-propene d. NOTA 19. The correct name of 2-tert-butylpentane a. 2-tert-butylpentane c. 2-butylpentane b. 2,2,3-trimethylhexane d. 4,5,5-trimethyl hexane 20. The correct name of 2-ethyl-3-methyl-5-isoprpylhexane a. 4,5-dimethyl-2-heptanol b. 3,4-dimethyl-6-heptanol c. 2,3,5,6-tetramethyloctane d. 2-ethyl-3-methyl-5-isoprpylhexane 21. The IUPAC name of the following compound is H3C H3C CH3 CH3 a. bicyclo[5.5.0]dodecane b. 3,8-dimethylbicyclo[4.4.0]decane c. 4,5-diethyloctane d. 2,3-dipropyl hexane 22. Molecule with the formula of C5H12 that only has primary hydrogen atoms. a. neopentane b. 2-methylbutane b. cyclopentane d. NOTA 23. Which of the following compounds will not exhibit resonance structure? a. CO2 b. SO3 c. SO4 d. NO3 For items # 24-31, identify whether the following pairs are a. the same compound b. Structural isomers c. Stereoisomers d. totally different compound 24. 25. 26. 27. 2| 28. 29 30. 31. 32. Which of the following compounds cannot exhibit cis-trans isomerism a. CH2= CHCH2CH3 b. CH3CH2CH = CHCl b. CH3 CH= CHCH3 d. NOTA For items # 33-37, identify the functional group present as a. Primary b. Secondary c. Tertiary d. Quaternary 33. 35. OH CH3 34. OH 36. NHCH3 NH2 37. CH3CH2NHCH2CH3 For items # 38-42, decide which member of each of the following pairs has the higher boiling point? 38. 39. 40. 41. 42. a. ethane c. hexane a. propane c. gasoline a. pentane b. d. b. d. b. chloroethane pentane propanamine Ethanol neopentane Identify the IUPAC name of the following molecular structure. 43 a. cis – 2,4 - Dimethylpentane b. trans – 2,4 - Dimethylpentane c. 2,4 - Dimethylpentane d. 1,1,3,3 - tetramethylpropane Identify the correct molecular structure of the following molecular formula. 44. a. Neopentyl chloride b. c. 3| 45. sp2 hybridization will yield a. 1 π bond and 3 σ bond c. 3 π bond and 1 σ bond b. 2 π bond and 2 σ bond d. 4 σ bond 46. sp hybridization will yield a. 1 π bond and 3 σ bond c. 3 π bond and 1 σ bond b. 2 π bond and 2 σ bond d. 4 σ bond 47. Which of the following DONT EXPERIENCE a restricted rotation ? a. alkane b. alkene c. alkyne d. alkenol 48. The geometric shape of methane is a. tetrahedral c. bent b. trigonal planar d. linear 49. The geometric shape of water is a. tetrahedral c. bent b. trigonal planar d. Linear 50. Which of the following bond is most polar ? a. C – C b. C – H c. C – O d. C – F 51. What is the force of attraction caused by permanent dipole moment of a molecule ? a. Ion-ion forces b. Dipole – dipole forces c. H- bond d. Van der Waals 52. What is the force of attraction caused by temporary dipole moment of a molecule ? a. Ion-ion forces b. Dipole – dipole forces c. H- bond d. Van der Waals 53. Which of the following compounds CANNOT exhibit geometric isomerism ? a. alkenes b. cycloalkanes c. cycloalkenes d. Alkynes 54. What is the only alcohol used in beverages ? a. ethyl alcohol c. methanol b. methyl alcohol d. isopropyl alcohol 55. What is the simplest hydrocarbon ? a. methane c. formaldehyde b. ethane d. methanol 56. As suggested by its name, an infrared spectrometer uses infrared electromagnetic radiation in its machine. This infrared radiation will result in which molecular activity? a. molecular rotation b. molecular vibration c. molecular movement d. molecular ionization 57. Which of the following is 4-methylpentan-1-ol? a. b. c. d. 58. Which is 3,3-dimethylbutan-2-ol? a. b. c. d. 4| 59. a. b. c. d. Diethyltrimethyldipropyldecane 2-methyl-2-propyl-3-ethyl-3-propyl-4-propyl-5-ethyl-5propylhexane 3,5-diethyl-2-methyl-2,3,4,5-tetrapropylhexane 4,6-diethyl-4,7,7-trimethyl-5,6-dipropyldecane II. Identify the functional groups that produces peak at the identified wavelength. 5| Prepared by: Prof. Richard M. Valencia 6|