Partial Periodic Table
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1 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 unauthorized assistance. 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 ziplock bag. Please put all you answers on the test. Use the backs of the pages for scratch. PLEASE read the questions very carefully! PLEASE legibly print your name on each page of the exam. Partial Periodic Table A 8A H He A 3A 4A 5A 6A 7A Li Be B C N O F Ne Na Mg 3 Al 4 Si 5 P 6 S 7 Cl 8 Ar I Page of 8
2 (0 pts) a) The carbon atoms of the two perspective chair ( flip chair ) conformations of cyclohexane are given below. One of the carbons is labeled (carbon ) in both structures, and one of the H atoms on carbon is shown, and circled, in the structure on the left. Carefully complete the two structures showing ALL H atoms. Circle the H atom on the right structure corresponding to the H atom circled on the left structure. Use a broken line to indicate if a C H is behind one of the C C bonds, and make an unambiguously bold line if a C H bond is in front of one of the C C bonds. H b) Complete the two flip-chair conformations for cis-,4-dimethylcyclohexane, using the carbon atom numbering scheme indicated. Do not put in the H atoms on the rings, but use CH 3 to indicate the methyl groups. In the boxes below the structures, write the estimated strain energy for each conformation in units of GB = Gauche Butane interactions a single,3-diaxial CH 3 H interaction. Page of 8
3 ) continued- c) Complete the two flip-chair conformations for trans-,4-dimethylcyclohexane and give the strain energy of the two conformations as in part b) above. d) Which stereoisomer of,4-dimethylcyclohexane is more stable, cis or trans? e) Complete the two flip-chair conformations for trans-,-dimethylcyclohexane and give the strain energy of the two conformations as in part c) above. Page 3 of 8
4 ) (0 pts) Give the single major product for each of the following reactions (two major product for part e), carefully showing stereochemistry using wedges and dashes. If a racemate is formed, show only one enantiomer and label it rac. Assume chiral starting materials are single pure enantiomers unless they are labeled rac. NOTE: Ph = phenyl group = benzene ring. a) NaCN EtOH b) F equivalent NaI acetone c) Ph O t-buoh d) H O EtOH e) CH 3 OH Heat Give the TWO major products for part e Page 4 of 8
5 3) (0 pts) Propose reagents for accomplishing each of the following reactions. Make your reaction efficient (i.e. the target product should be the major product). Assume chiral starting materials and products are single pure enantiomers unless they are labeled rac. If the solvent is important to obtain the product, then include the solvent along with the reagents. If you need an organometallic reagent, you can use it without showing how to make it. a) I F b) c) d) e) S Page 5 of 8
6 4) (0 pts) Dimethyl sulfoxide (DMSO) is a favorite solvent for organic reactions. The structure is typically written as follows. O H 3 C S CH 3 This is NOT a valid valence bond structure, but rather an historical holdover that refuses to go away. a) Draw a valid valence bond structure for DMSO, showing all lone pairs and formal charges. b) Categorize DMSO as a solvent (choose from: polar or apolar: protic or aprotic; donor or non-donor). c) What is the hybridization of the S atom in DMSO? d) Which is the stronger nucleophile in DMSO, sodium methoxide or sodium thiolate? e) Which is the stronger nucleophile in methanol solvent, sodium methoxide or sodium thiolate? Page 6 of 8
7 4) continued- f) When the bromothiol is treated with one equivalent of methoxide in DMSO, one product is formed in high yield. The product has molecular formula C 5 H 0 S, and there is no double bond. Also, as you can tell from the molecular formula of the product, there is no oxygen atom. Carefully draw the structure of the product, showing stereochemistry if appropriate. H S equivalent of CH 3 O DMSO g) The fact that the CH 3 O group did not end up in the product is interesting. Give a very brief explanation for why there is very little substitution with methoxide in this reaction. Page 7 of 8
8 5) (0 pts) a) Give a reagent for converting methanol in THF solvent to sodium methoxide in THF. CH 3 OH THF solvent CH 3 O Na b) Treatment of (S,S)--bromo--methylcyclohexane () with sodium methoxide in THF gives two products: Alkenes and 3. Circle the major product. CH 3 O CH 3 OH THF solvent 3 c) Carefully complete the energy diagram below, showing the energetics of the system leading from starting material, to products and 3. Page 8 of 8
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: 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: 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
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 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
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: 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
Partial Periodic Table
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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
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 1A
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