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Exam S2012-V1.pdf

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Paul Harrison

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Name:_________________________                      Student Number: ____________________________   th CHEM / CHEMBIO  2OA3          Midterm Test       VERSION 1             May 24 , 2012   Instructors: J.Landry, G.Bahun  Duration: 120 min     Name    Student Number    Laboratory Section  Exempt  L03  L05  L07  (Circle)  L02  L04  L06  L08    Laboratory Station  (Example 0 – 72)    Instructions: This examination paper consists of 22 pages, containing 20 multiple choice (MC) questions, and 8 short-answer questions. You are responsible for ensuring your copy of the question paper is complete. A periodic table is provided on the last two pages. Models kits are permitted. Answer all the MC questions on the optical scan sheets. Each MC question is worth two 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. 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 of this page, by filling in the BUBBLE in the “version” column provided. You MUST sign the sheet in the space provided. 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. You MUST also complete ALL the information at the top of this page. MC Q21 Q22 Q23 Q24 Q25 Q26 Q27 Q28Total /40 /5 /2/4 /6 /6 /10 /7 /5 /85 1    Name:_________________________                      Student Number: ____________________________   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 bubble 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 will NOT be sensed. Erasures must be thorough or the scanner will still sense a mark. Do NOT use correction fluid on the sheets. Do NOT put any unnecessary marks or writing on the sheet. 1. On SIDE 1 (red side) of the form, in the top box, print your student number, name, course name, and the date in the spaces provided, in pen. Then you MUST write your signature, in the space marked SIGNATURE. 2. In the second box, mark your student number and test or exam version number (1, 2, 3 …) by filling in the corresponding bubbles underneath, in pencil. 3. Answers: mark only ONE choice from the alternatives (A,B,C,D,E) provided for each question. 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 number on the test paper. Begin answering Question # 1 using the first set of bubbles, marked “1”. Do Not use Side 2.   2    Name:_________________________                      Student Number: ____________________________   Multple Choice (use scantron to answer): Version # 1  Questions 1 to 20: 2 Marks each (40 Total)  1. Consider the imine drawn below. The lone pair of electrons on the nitrogen would be in what type of orbital? 2 A) sp B) sp C) s 3 D) sp E) p 2. How many lone pair of electrons exist in the following molecule? O –O NH + 3 A) 3 B) 4 C) 5 D) 6 E) 2 3. Which of the following diatomics would have the greatest theoretical bond order from a molecul+r orbital perspective? A) H 2 B) HeLi C) HHe + D) He 2 E) LiH + 3    Name:_________________________                      Student Number: ____________________________   4. Which of the following orbitals are capable of making a pi bond together. A) p & p B) sp & p C) sp & p 3 D) sp & p E) all of the above 5. How many isomers (including stereoisomers) exist for a molecule with molecular formula C 4 C9? A) 8 B) 3 C) 5 D) 7 E) 9 4    Name:_________________________                      Student Number: ____________________________   6. Convert the following cyclohexane chair structure into a flat ring structure. A) B) C) D) E) 5    Name:_________________________                      Student Number: ____________________________   7. What name does not accurately describe the following molecule? A) 4- isopropyl-3-methylbutanol B) 2,4-dimethlyhexanol C) 3-( isobutyl)butan-1-ol D) 2,4-dimethyl-6-hydroxyhexane E) 3,5-dimethylhexan-1-ol 8. Which would be the most acidic proton in the following molecule A) H b B) H d C) H a D) H e E) H c 6    Name:_________________________                      Student Number: ____________________________   9. If the following molecule were to be deprotonated, which of the following resonance structures would be the highest contributor to the overall structure. A) B) C) D) E) They would all be equal contributors. 7    Name:_________________________                      Student Number: ____________________________   10. Which of the following compounds would be least likely to lose a proton when exposed to a base. A) propyne B) propanone C) propanal D) propanol E) propene 11. The following two molecules have what relationship? A) Constitutionailsomers B) Enantiomers C) Meso isomers D) Thesamemolecule E) Diastereomers 12. Choose the incorrect statement regarding stereoisomers. A) If molecule has a mirror plane of symmetry, regardless of stereocentres, it will not be optically active. B) Diastereomers will have the same melting point. C) A carbon with 4 unique substituents will be a stereogenic center D) 3-methylpentane is not chiral. E) There is no need to identify the stereochemistry of propene. 8    Name:_________________________                      Student Number: ____________________________   13. Consider the molecule below. Which bromine would be most likely to leave as a bromide from the molecule? A) Br 5 B) Br 3 C) Br 4 D) Br 1 E) Br 2 14. Which of the following statements regarding electrophiles or nucleophiles are incorrect. A) An electrophillic center exists on an atom with a partial negative charge. B) A nucleophile should have an easily accessible lone pair of electrons. C) The carbon in a carbonyl group is generally a good electrophile. D) Me NH can act as a nucleophile. 2 E) In the substitution of a alkylhalide with hydroxide to yield an alcohol, the nucleophile is the hydroxide. 15. The enantiomer of the following molecule would have what configuration? (Label the stereo-centres from left to right) A) R,R,R B) S,S,S C) S,R,S D) R,R,S E) S,R,R 9    Name:_________________________                      Student Number: ____________________________   16. A student is transforming propionitrile (CH CH CN) i3to a2carboxylic acid (CH C3 COO2) by acid hydrolysis, a reaction you will learn next term. Even though they were told the reaction would take about 6 hr, they want to observe the reaction by monitoring the IR spectra of the reaction mixture at various times. Which of the following is true? -1 A) As soon as a peak is visible at 1700 cm the reaction is complete B) At time (t) = 0, there will be a peak around 2100 cm and no peak around 1700 cm - 1 C) At t = 3 hr, there will be a peak halfway between 2100 cm and 1700 cm , and the -1 -1 peak at 2100 cm will be half its original h-1ght D) The appearance of a peak at 2100 cm and disappearance of the peak around 1700 cm shows the reaction is complete -1 E) The C-H stretch for an sp hybridized carbon around 3300 cm should be used in
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