Test 1 a - HNWEK Kev , VEKSIONS l, 2 '53 CHEM ZOAS Test 1...

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Unformatted text preview: HNWEK Kev , VEKSIONS l, 2 '53 CHEM ZOAS Test 1 October 13, 2004 VERSION 3 Duration: 90 minutes Instructors: Drs. Harrison and Valliant Instructions: This examination paper consists of 12 pages and 50 multiple choice questions. Each question is worth one mark. You are responsible for ensuring your copy ofthe question paper is complete. The infrared correlation chart is provided on the last page. Answer all the questions on optical scan sheets. There are no part marks and you will not be penalized for incorrect answers. Follow the instructions on the optical scan sheets, and the University rules for OMR exams which are reproduced on page 2. Failure to follow instructions may result in loss of credit. Scan sheets will not be re- marked under any circumstanCes. You are responsible for ensuring all answers are in the correct place, and that you follow the correct procedure for filling out the scan sheet. Print your name, student number, course name, section number and date in the spaces provided on page I ofthe form. Section 01 is Dr. Valliant’s group; section 02 is Dr. Harrison’s. You MUST Sign the sheet in the space marked signature. Mark your student number in the space provided on the sheet on Side 1 AND FILL IN THE CORRESPONDING BUBBLES UNDERNEATH. Now enter your version number, which can be found on the top right hand corner ofthis page, by filling in the BUBBLE in the “version” column provided. Finally, BUBBLE in your section number. Now CHECK all of your entries. Begin answering questions using the first set of bubbles, marked "1". Note that questious 26-50 are also answered on side 1: DO NOT USE SIDE 2. All McMaster rules and procedures relating to Academic Dishonesty and Academic Integrity apply to this exam; all violations will result in a penalty. Students must do their own work. A program designed to detect similar answers will be used for this exam. Continued on next page OMR EXAMINATION — STUDENT INSTRUCTIONS NOTE: IT IS YOUR RESPONSIBILITY TO ENSURE THAT THE ANSWER SHEET IS PROPERLY COMPLETED. YOUR EXAMINATION RESULT DEPENDS UPON PROPER ATTENTION TO THESE INSTRUCTIONS. The scanner, which reads the sheets, senses the shaded areas by their non-reflection of light. A heavy mark must be made, completely filling the circular bubble, with an HB pencil. Marks made with a pen or felt-tip marker will NOT be sensed. Erasures must be thorough or the scanner may still sense a mark. Do NOT use correction fluid on the sheets. Do NOT put any unnecessary marks or writing on the sheet. 1. Print your name, student number, course name, section number and the date in the space provided at the top of Side 1 (red side) of the form. Then the sheet MUST be signed in the space marked SIGNATURE. 2. Mark your student number in the space provided on the sheet on Side 1 Ed fill in the corresponding bubbles underneath. 3. Mark only ONE choice from the alternatives (1,2,3,4,5 or A,B,C,D,E) provided for each question. If there is a Truex’False question, enter response 1 (or A) as True, and 2 (or B) as False. The question number is to the left of the bubbles. Make sure that the number of the question on the scan sheet is the same as the question number on the test paper. 4. Begin answering questions using the first set of bubbles, marked “1”. Continued on next page Part I: Orbitals Questions numbers 1—5 in this part relate to the orbitals which are sketched below. These include both atomic and molecular orbitals associated with the atom(s) marked “A”. Answer questions 1-5 based on these pictures: 1. Which letter corresponds to an ato ' _.- orbital? (A) b (B) d (C) 6 _ \_ g (B) h 2. Which letter corresponds to a 0' bonding molecul ' al? (A) C (B) 6 (C) f (D) 11 j 3. Whic ' r corresponds toam molecular orbital? (M0 e (or (Dlh (Bi 4. Which letter corresponds to the hybridized orbitals on a carbon atom in an alkene? (A) a (B) b (C) d (D) g © h 5. Which letter correspo 0 an sp3 hybridized atomic orbital? (A) a (B) b d (D) g (B) h Continued on next page Part II: Acyclic alkanes Questions numbers 6-13 in this part relate to the five hydrocarbons containing 7 carbon atoms shown as A-E below. Answer questions 6-13 using these structures: Ax/LA 6. Which compound is 2,4-dimethylpcntane? (A) A (B) B (C) C (D) D E 7. Which compound has a tert-butyl gr (A) A (B) B (C) C @ D (E) E 8 Which compound has five (5) methylene groups? A (B) B (C) C (D) D (E) E 9. Which compound(s) hasfhave a plane of symmetry perpendicular to the plane of the paper? (A) A (B) B&C(C) C&D(D) E @ A&E 10. Which compound is ‘ '7 (A) A (B) B C (D) D (E) E 11. Which compound has aquaternary c --u atom? (A) A (B) B (C) c D (E) E - Which compound has the highest melting point? @ A (B) B (C) C (D) D (E) E 13. The following sentence has the fomiat “Statement l BECAUSE Statement 2”. Decide whether statement 1 is true, whether statement 2 is true, and whether the REASON ING (the “because” relationship) between them is valid. “Compound A has the highest boiling point BECAUSE hydrocarbon molecules are only held together by weak, dispersive forces”. Statement 1 and Statement 2 are both correct, but the reasoning is NOT valid. Statement 1 is correct, but Statement 2 is NOT correct. (D) Statement 1 is NOT correct, but Statement 2 is correct. (E) Statement 1 and Statement 2 are both NOT correct :3 Statement 1 and Statement 2 are both correct, and the reasoning is valid. Continued on next page Part [11: General Questions 14—23 relate to the following reaction, in which ketene(1) reacts with compound (2) to give compound (3). Tetrahydrolipstatin (3) is sold as an anti-obesity drug under the trade name Orlistat. 23 El H C H T .v“ 1t 23 _,.. \r b O O O 0 i H N H (1) (2) (3) 14. What is the hy " ation of the carbon atom marked “2” in ketene (1)? (A) sp sp2 (C) sp3 (D) no hybridization (E) p sp - (B) 3})2 (C) Sp3 (D) no hybridization (E) p 16. What functional group is marked a in com - - (2)? (A) ketone (B) alcohol (C) ester ldehyde (E) amide 1?. What functional group is mawin compound (2)? 15. is the hybridization of the carbon atom marked “1” in ketene (l )? (A) ketone (B) alcohol ster (D) aldehyde (E) amide 18. What functional group is marked c in compound (2)? (A) ketone (B) alcohol (C) ester (D) aldehyde @amide 19. What term best describes the relationship of the substituents on the 4-membered ring in product (3)? (A) axial (B) cis (C) equatorial ® trans (E) unrelated 20. - . many chiral (i.e. stereogenic) centres are present in compound (1 )? 0 (B) 1 (C) 2 (D) 3 (E) 4 21. How many chiral (i.e. stereogenic) centres are present in und (3)? (A) O (B) 1 (C) 2 (D) 3 4 22. How many lone pairs of ele are present in ketene (1)? (A) 0 (B) 1 © 2 (D) 3 (E) 4 23. Which of the following best describes the dipole in the group marked (2)? RCHZ CH2—1—> RCH2 4——1— ROI-12 (A) >201 >=o (e) >=o (D) >201 (E) no dipole H H H H Continued on next page Part IV: Resonance (Questions 24 and 25) 24. indicate which of the following structures represents the most stable resonance form of the structure marked “1” below: 0 ,0" ,o o —< ac: —c; 4 orig—<0 CHI—<0 0 0‘ \0+ " o+ 0—H (1) (A) (3) ® (0) (E) 25. How many stable resonance forms of equal energy are there in the sulfite anion ($032")? (the core structure below is provided as a help, but does not show all bonds and charges) 0 2- (A) 0 (B) 1 (C) 2 3 (E) 4 Part V: Cycloalkanes and Conformations Questions 26 and 2? relate to compounds 1 and 2: Br CH3 firms wBr H H 1 2 26. Compounds 1 and 2 are: (A) structural isomers (B) identical rotational isomers n a ay (D) both (A) and (B) (E) not related i 27. ompound 1, the relationship between the bromine and methyl groups are: @ cis (B) trans (C) anti (D) eclipsed (E) parallel 28. In the lowest energy chair conformation of cis- l -amino-2-t-butylcyclohexane, the two substituents are related in the following way: (A) both are axial 8 both are equatorial @ the amine is predominantly axial - the amine is predominantly equatorial (E) none of the above Continued on next page 29. In the lowest energy chair conformation of trans-4—fluoro-l-cyclohexanol, the fluorine and alcohol substituents are related in the following way: ‘ both axial fl) both equatorial only the fluorine is axial (D) only the amine is equatorial (E) none of the above 30. a 00m temperature, the two chair conformations of cis-1,4-dimethylcyclohexane: @ are equally pOpulated are unequally populated (C) have two axial substituents (D) have two equatorial substituents (E) (B), (C), and (D) 31. At room temperature, the two chair conformations of cis-l ,3—dimethylcyclohexane: : are equally populated (E), are unequally populated have two axial substituents have two equatorial substituents (B), (C), and (D) H H;f 3 4 32. Compound 4 is more stable than compound 3 because of a change in: (A) hybridization bond angle coulombic repulsion size (E) both (B) and (D) CH3 Km 5 33. The correct planar structure for compound 5 is: Continued on next page to 0’ F ""F a F D H O «««« ,, e F Questions 34-36 relate to the structure of menthol: CH3 CL 6 ; OH /\ 34. The predominant form of menthol in solution has: (A) the isopropyl group equatorial (B) the hydroxyl group axial (C) the hydroxyl group equatorial the methyl group axial (A) and (C) 35. Which of the following statements are true? (A) menthol is achiral menthol has a plane of symmetry fi menthol does not have a plane of symmetry menthol has a total of two stereocenters (E) both (C) and (D) 36. The absolute configuration at the carbon bearing the substituent that is going into the plane of the paper is: A R S its not a stereocenter (D) P (E) (C) and (D) 3?. What is the relationship between the following compounds? Mk/ (A) stereoisomers conformational isomers @ structural isomers identical (E) enantiomers Continued on next page 38. What is the relationship between the following compounds? E C} CI CI CI Et A rotational isomers ‘33) stereoisomers structural isomers (D) identical (E) both (A) and (C) 39. What is the relationship between the following compounds? Hwy (A) rotational isomers (B) no relationship structural isomers identical (E) both (A) and (C) Part VI Newman Projections and IR Questions 40-42 pertain to the following Newman projections: R CI R a R K CI 29: R: isopropyl CI CI A B C D E 40. Which of the Newman projections represent ' 'hest energy conformer? (A) A (B) B (C) C D (E) E 41. In which of the Newman projections are the ‘ argest groups eclipsed? (A) A (B) B (C) C @ D (E) E 42. '. ' h of the Newman projections has the largest Gauche interaction? A (B) B (C) C (D) D (E) E Continued on next page Questions 43 to 45 are based on the following IR spectrum. 43. 44. \\'.:\ <2: ac!!! Inn. 7 59000 6*th l th; $00 Which of the followi o notional groups are n_ot evident in the spectrum? (A) ester m terminal alkyne (C) ketone (D) anhydride (A), (C) and (D) Which of the following functional groups are evident in the spectrum? (A) ester terminal alkyne (C) ketone (D) anhydride (A), (C) and (D) 45. u e strong peak at highest energy represents: m) sp‘ C-H groups (B) sp2 OH groups (C) alcohol OH I aldehyde C=O group (E) the finger print region Questions 46 to 48 relate to the following IR spectrum 46. we g . . u u g 1 t2: n q “‘ (nrflq Micromeiers 25 3 4 5 E ‘4' B 11 12 13 III. 15 I I I g u hm“ l l I . 1200 3200 2800 2400 2000 1300 1500 WOO 1m!) BBB SW 400 Wavenumber {cm-1) 3500 Which of the following functional groups are n_0t evident in the spectrum? (A) ester anhydride (C) ketone (D) terminal alkyne (A), (B) and (C) Continued on next page 10 4?. Which of the following functional groups are evident in the spectrum? (A) ester (B) anhydride ketone terminal alkyne - (A), (B) and (C) 48. The strong peak at highest energy represents: : sp‘ C-H group(s) (E) Sp C-H groupts) OH group(s) (D) aldehyde C=O group(s) (E) water 49. To have a peak in the IR spectrum: the bond must be weak the bond must be strong there must be a rhythmical change in dipole moment there must be a rhythmical change in polarizability the bond must be polar 50. The finger print region occurs: (A) above 3000 cm" (B) between 2500 and 2000 cm" (C) between 1500 and 2000 cm" between 400 and 500 cm"1 somewhere below 1600 cm'] Continued on next page IR Correlation Table: Typical IR Absorption Frequencies For Common Functional Groups Bond Functional Group Frequency in cm'l (lntensity*) C-H Alkane 3000—2850 (s) -CH3 1450 and 1375 (m) -CH2- 1465 (m) Alkene 3100-3000 (m), 1000-650 (3) Aromatic 3100-3050 (s), 900-690 (s) Alkyne (terminal) 3300 (s) Aldehyde 2850 and 2750 (w) C=C Alkene 1630 (w-m) Aromatic 1600—1413 (w-m) C-C Alkyne 2150-2100 (w-m) C=O Aldehyde 1740-1120 (5) Ketone 1725-1105 (s) Carboxylic Acid 1?30-1?00 (S) Ester 1150-1130 (s) Amide 1610-1640 (s) Anhydride 1810 and 1760 (3) Acid Chloride 1800 (s) C-0 Alcohol, Ether, Ester, 1300-1000 (5) Carboxylic Acid, Anhydride 0-H Alcohol, Phenol Free 3650-3600 (m) Hydrogen-bonded 3500-3200 (m) Carboxylic Acids 3300-2400 (m) N-H Primary and Secondary 3550-3060 (m-s); 1640-1550 (m-s) Amine and Amide C-N Amine 1250-1000 (m-s) C=N lmine and Oxime 1690-1640 (w-s) C=N Nitrile 2260-2240 (m) N=O Nitro (R-NOz) 1550 and 1350 (s) C-Cl Chloride 800-600 (s) * s = strong; m = medium; w = weak THE END ...
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Test 1 a - HNWEK Kev , VEKSIONS l, 2 '53 CHEM ZOAS Test 1...

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