Partial Periodic Table
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1 Easily Legible Printed Name: CEM 3351 (100), Fall 2015 Professor Walba First our Exam September 22, 2015 CU onor Code Pledge: n my honor, as a University of Colorado at Boulder Student, I have neither given nor received unauthorized assistance. scores: 1) 2) 3) 4) 5) Signature: Recitation TA Name: Recitation day and time: This is a closed-book exam. The use of notes, calculators, scratch paper, or cell phones will not be allowed during the exam. You may use models brought in a clear Ziploc bag. Please put all your answers on the test in the appropriate place. Use the backs of the pages for scratch (there are two additional blank scratch sheets after the last page of the exam). D NT PUT ANSWERS N TE SCRATC SEETS. PLEASE read the questions very carefully! PLEASE legibly print your name on each page of the exam. Partial Periodic Table 1A 8A 1 2 e 2A 3A 4A 5A 6A 7A Li Be B C N F Ne 11 Na 12 Mg 13 Al 14 Si 15 P 16 S 17 Cl 18 Ar 35 Br 53 I Page 1 of 8
2 1 (20 pts) a) For 2,4-dimethylpentane (structure shown at right), let the eclipsed conformation shown in the Newman projection on the energy diagram below be defined as the 0 dihedral angle. Draw Newman projections of the three staggered conformations of 2,4- dimethylpentane sighting down the C2-C3 bond, in the boxes. Please rotate the front carbon clockwise moving from 0 to 60, 180, and 300. Complete the energy diagram by indicating the relative energy of all the conformations (eclipsed, staggered, and everything in between) in the rotation from 0 to 360 = 0 using a smooth curve. 2 3 Page 2 of 8
3 1 continued b) Give the degree of substitution (1, 2, 3, or 4 ) for carbons 1 5 (the main chain) of 2,4-dimethylpentane c) Draw skeletal structures (molecular graphs NT showing the hydrogens) of all possible isomers (constitutional isomers and stereoisomers) for hydrocarbons with the molecular formula C 4 8. Draw each isomer only once. Points will be deducted for missing structures, and for drawing the same structure more than once. Page 3 of 8
4 2) (20 pts) Draw skeletal structures of the following compounds carefully showing stereochemistry where appropriate. a) 2-Chlorobutane b) (E)-2-Bromo-3,4-dimethyl-2-pentene c) (Z)-2-Chloro-2-butene d) (E)-4-Isopropyl-4-octene e) 3-Bromo-5-chloro-2-methylheptane f) Isobutylcyclohexane 2f) For the pair of isomers indicated below, circle the molecular structure of the isomer with the highest standard heat of formation ( F ). 1 2 g) Which isomer in part 2f) is more stable, 1 or 2? h) Give a very brief explanation (it has to fit in the box below) for why your choice in part 2g) is more stable. Page 4 of 8
5 3) (20 pts) a) For each of the following structures, indicate the correct formal charge on each atom (following normal convention, don t indicate 0 on an atom if it has no formal charge). Assume all valence electrons are shown. C 3 C 3 C 3 C 3 3 C C C 3 C 3 3 C C C 3 3 C C C 3 N C 3 3 C C 3 N C 3 F F B C 3 C 3 C 3 F 3 C C C 3 C C C 3 C b) For each of the following pairs of compounds, circle the stronger Brønsted acid. C F N 3 F N 3 Page 5 of 8
6 4) (20 pts) a) With regard to the following equilibrium equation: 3 C + Br 3 C + Br i. Circle the molecules acting as Brønsted acids. ii. Which acid is stronger? (Use the compound number in the equation to indicate your choice). iii. Does the equilibrium favor the starting materials or the products? iv. Give the major reason why the stronger acid is stronger (e.g. compound x is the stronger acid because ). b) With regard to the following equilibrium equation: 3 C + 3 C N 3 C + 3 C N i. Circle the molecules acting as Brønsted acids. ii. Which acid is stronger? (Use the compound number in the equation to indicate your choice). iii. Does the equilibrium favor the starting materials or the products? iv. Give the major reason why the stronger acid is stronger (e.g. compound x is the stronger acid because ). Page 6 of 8
7 5) (20 pts) a) Give the structure of the major product obtained in the following reaction. a) Br b) Propose an arrow-pushing mechanism for the reaction in part 5a) above. Each of the following reactions proceeds in one step, with no reactive intermediates involved. Propose an arrow-pushing mechanism for each reaction. c) C C + Br + Br Page 7 of 8
8 5 continued d) Br Br e) + Page 8 of 8
Partial Periodic Table
Easily Legible Printed Name: CEM 3311 (300), Fall 2014 Professor Walba First our Exam September 23, 2014 scores: 1) 2) 3) 4) 5) CU onor Code Pledge: n my honor, as a University of Colorado at Boulder Student,
Partial Periodic Table
CEM 33-00, Fall 203 Professor Walba First our Exam September 24, 203 scores: ) 20 2) 20 3) 20 4) 20 5) 20 CU onor Code Pledge: n my honor, as a University of Colorado at Boulder Student, I have neither
Partial Periodic Table
Easily Legible Printed Name: CHEM 3351 (100), Fall 2016 Professor Walba Second Hour Exam October 18, 2016 CU Honor Code Pledge: On my honor, as a University of Colorado at Boulder Student, I have neither
Partial Periodic Table
Easily Legible Printed Name: CHEM 3451, Spring 2018 Professor Walba Second Hour Exam March 13, 2018 scores: 1) 2) 3) 4) 5) CU Honor Code Pledge: On my honor, as a University of Colorado at Boulder Student,
Partial Periodic Table
Easily Legible Printed Name: CEM 3351 (100), all 2015 Professor Walba Third our Exam November 17, 2015 scores: 1) 20 2) 20 3) 20 4) 20 5) 20 100 CU onor Code Pledge: n my honor, as a University of Colorado
Partial Periodic Table
CEM 33, Fall 00 Professor Walba Third our Exam November 8, 00 Scores: ) 0 ) 0 3) 0 4) 0 5) 0 00 CU onor Code Pledge: n my honor, as a University of Colorado at Boulder Student, have neither given nor received
Partial Periodic Table
Easily Legible Printed Name: CEM 3351 (100), Fall 2015 Professor Walba econd our Exam ctober 20, 2015 CU onor Code Pledge: n my honor, as a University of Colorado at Boulder tudent, I have neither given
Partial Periodic Table
CHEM 33-00, Fall 03 Professor Walba Third Hour Exam November 9, 03 scores: ) ) 3) 4) 5) CU Honor Code Pledge: On my honor, as a University of Colorado at Boulder Student, I have neither given nor received
Partial Periodic Table
Printed ame: CEM 3371, Spring 2015 Professor Walba First our Exam March 10, 2015 CU onor Code Pledge: n my honor, as a University of Colorado at Boulder Student, I have neither given nor received unauthorized
Partial Periodic Table
CEM 3311, Fall 2011 Professor Walba Third our Exam November 17, 2011 scores: 1) 20 2) 20 3) 20 4) 20 5) 20 100 CU onor Code Pledge: n my honor, as a University of Colorado at Boulder tudent, I have neither
Partial Periodic Table
Easily Legible Printed Name: CHEM 3351 (100), Fall 2016 Professor Walba Third Hour Exam November 15, 2016 CU Honor Code Pledge: On my honor, as a University of Colorado at Boulder Student, I have neither
Partial Periodic Table 1A
CEMISTRY 3311, all 2001 Professor Walba irst our Exam September 27, 2001 scores: 1) 20 2) 20 3) 15 This is a closed-book "open model" exam. You may use models, but no notes or books. Please put all your
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