Fall 2004 Chem 266 1Course Number CHEMISTRY 266 Course Title INTRODUCTORY ORGANIC CHEMISTRY Instructors J. M. CHONG, S. FORSEY Date of Exam January 7, 2005 Time Period 2:00 – 5:00 PM Duration of Exam 3 HOURS Number of Exam Pages (including this cover sheet) 16 Exam Type CLOSED BOOK Additional Materials Allowed CALCULATORS, MOLECULAR MODELS INSTRUCTIONS1. On the computer card, fill in the best choice Ato Dfor each of the 50 questions which follow. 2. There is 1 mark for a correct answer and 0 marks for an incorrect or missing answer. 3. Under ID number, put your ID number. 4. Under section, put 001 (for Dr. Chong’s section) or 002 (for Dr. Forsey’s section). Do not leave blank. 5. Under Card Number, leave blank. 6. Remember to put your name and course number on the right. 7. Calculators and/or molecular model kits may be used by individual students but may not be shared around during the examination period. 8. Make certain that all of your answers are properly indicated on the computer card. Only the answers marked on the computer card will be considered in arriving at your final exam mark. Do not submit the question papers. 9. The following abbreviations may appear: D = deuterium, 2H Et = ethyl, C2H5Me = methyl, CH3Ph = phenyl, C6H510. A Periodic Table of the Elements appears on the last page of this examination.
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Fall 2004 Chem 266 21. For the following species, charges are shown but lone pairs and single electrons are not. The pair of species (1) to (4) which have the same number of valence electrons is: (1)(2)(3)(4)NH3CH3BH3H2SA(1) and (2) B(1) and (3) C(1) and (4) D(2) and (3) 2. In the hydrazone of formaldehyde, H2CNNH2, the bond angles around the carbon atom and the nitrogen atom bearing no hydrogens are, in that order, closest to: A109.5º, 180º C120º, 109.5º B109.5º, 109.5º D120º, 120º 3. Consider the following structures. The one(s) that is(are) NOT valid contributing resonance structures of resonance stabilized anions is: OCOOOCHOCNOOHH(1)(2)(3)(4)H2CCH2HA(4) only B(2) and (4) C(3) only Dnone of the above (all are valid structures) 4. A molecular dipole is to be expected only in: ASO3CCH2F2BBeF2Dnone of the above