CHEM 3311 Exam 2 ANSWER KEY
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1 CEM 3311 Exam 2 ANSWER KEY March 11, 2014 Time: 2 ours Please sign the onor Pledge h in this sheet with your scantron. I pledge that n my honor, as a University of Colorado-Boulder student, I have neither given nor received unauthorized assistance on this work. PRINT YUR FULL NAME SIGN ERE General Instructions n the computer graded answer sheet, enter bubble LAST NAME, FIRST, Middle Initial STUDENT ID RECITATIN SECTIN ID (Write a zero before the recitation section number - for example, section 227 is written as 0227.) Answer all questions on the computer graded answer sheets by filling in the proper bubble with a No. 2 pencil. If you change an answer, erase the undesired mark thoroughly. Mark only the best answer to each question. Programmable calculators are not permitted during the exam. A section of the Periodic Table with atomic numbers masses is shown below. Use the back of the exam pages as scratch paper. There are 5 exam pages (with 25 questions), a cover page, two blank pages (scratch paper). When instructed to begin the exam, please check that you have all pages. Good luck! Please return the completed scantron sheet to the exam proctors. You may take the exam scratch paper with you. Recitation Section # Day of the Week Time of the Day TA 0113 Monday 12:00-12:50 PM Cindy White 0115 Monday 1:00-1:50 PM Cindy White 0123 Tuesday 12:00-12:50 PM Cindy White 0125 Tuesday 1:00-1:50 PM Cindy White 0127 Tuesday 4:00 4:50 PM Cindy White 0213 Monday 12:00-12:50 PM Zhenyi Jensen u 0215 Monday 1:00-1:50 PM Zhenyi Jensen u 0223 Tuesday 12:00-12:50 PM Tim Rochelle 0225 Tuesday 1:00-1:50 PM Tim Rochelle 0227 Tuesday 4:00 4:50 PM Tim Rochelle
2 CEM 3311, Exam 2, March 11, 2014 Page 1 1. Which alkene releases the smallest amount of heat on combustion? (A) 2-methyl-2-butene (C) (Z)-2-pentene (B) 1-pentene (D) (E)-2-pentene 2. Which of these constitutional isomers would produce one major product when reacted with Cl? (I) 2-methyl-1-butene (II) 3-methyl-1-butene (III) 2-methyl-2-butene (A) I II (B) II III (C) I III (D) I, II, III 3. For which constitutional isomer does a carbocation rearrangement account for the product distribution observed? (I) 2-methyl-1-butene (II) 3-methyl-1-butene (III) 2-methyl-2-butene (A) I (B) II (C) III (D) all of these 4. Which of these alkyl bromides cannot be synthesized using a Markovnikov addition of to an alkene? (A) (B) (C) (D) Correct Answer: A 5. Which alkene would not produce any of the target molecule (product) when reacted with Cl? Cl Target molecule Correct Answer: C 6. What is the stereochemical outcome of the reaction shown below? (A) There is no reaction. (B) An achiral compound is the major product. (C) A racemic mixture is obtained. (D) A diastereomeric mixture is produced.
3 CEM 3311, Exam 2, March 11, 2014 Page 2 7. Compound X on reaction with 2 in C 2 Cl 2 produced racemic 1,2-dibromobutane as the product. What is compound X? (A) 1-Butene (B) (E)-2-Butene (C) (Z)-2-Butene (D) 2-methylpropene 8. What is the stereochemical outcome of the reaction shown below? 2 C 2 C 2 Cl 2 (A) A racemic mixture is obtained. (B) A diastereomeric mixture is produced. (C) Constitutional isomers are formed. (D) The meso compound is formed. 9. Each alkene listed below is reacted with Cl 2 in C 3. Which alkene reacts at the fastest rate? (A) (E)-2-pentene (C) 2-methyl-2-butene (B) (Z)-2-pentene (D) 1-pentene 10. Select the best reaction conditions to accomplish the transformation shown below.???? racemic mixture (A) 1 M N 3 (B) ydroboration, followed by oxidation with 2 2, Na (C) (1) g(ac) 2, TF- 2 ; (2) NaB 4, Na (D) 2, Select the best reaction conditions to accomplish the transformation shown below.??? (A) (B) 2, C 2 Cl 2 (C) 2, 2 (D), (C 3 ) 3 C---C(C 3 ) 3
4 CEM 3311, Exam 2, March 11, 2014 Page Compound X is reacted with 3 in C 2 Cl 2, followed by hydrolysis in the presence of (C 3 ) 2 S. The structure of the only product formed is shown. What is the structure of compound X? Correct Answer: D 13. Assign the absolute configuration at each chiral center in compounds I II. C 3 C 3 (A) (I) R, (II) R (C) (I) R, (II) S I C 3 C C 2 II (B) (I) S, (II) S (D) (I) S, (II) R 14. D-glucose is one of several stereoisomers with the structural formula shown below: C-C-C-C-C-C 2 What is the maximum number of stereoisomers with this structural formula? (A) 4 (B) 8 (C) 16 (D) What is the relationship between the molecules shown? 3 C 3 C 3 C C 3 (D) omomers (identical)
5 CEM 3311, Exam 2, March 11, 2014 Page What is the relationship between the molecules shown? 3 C 3 C (D) omomers (identical) 17. What is the relationship between the molecules shown? Cl Cl (D) omomers (identical) 18. What is the relationship between the structures shown below? (D) omomers (identical) 19. Select all the statements that correctly describe enantiomers. (I) Enantiomers of a compound rotate the plane of polarized light by the same amount; one clockwise the other counterclockwise. (II) An equimolar mixture of enantiomers is optically inactive. (III) Enantiomers react with an achiral reagent at the same rate. (A) I II (B) I III (C) II III (D) I, II, III 20. Select the chiral molecule. Correct Answer: B
6 CEM 3311, Exam 2, March 11, 2014 Page Which reaction is best described by a concerted, one-step mechanism? (I) Reaction of 2-methylpropene with 1M N 3 (II) Reaction of 2-methylpropene with peroxyacetic acid (III) Reaction of 2-methylpropene with (A) I (B) II (C) III (D) none of these 22. Consider the mechanism for the reaction of 2-methyl-1-butene with in the presence of peroxides. Classify the intermediate carbon-centered radical formed during propagation. (A) Methyl radical (B) 1º radical (C) 2º radical (D) 3º radical 23. Which reaction conditions would best facilitate the transformation shown below??? (A) C 3 C 3 (peroxyacetic acid) in C 2 Cl 2 (B) 2 in 2 (C) Reaction with 3, followed by reaction with 2 2, 2 (D) Reaction with g(ac) 2 in TF- 2, followed by reaction with NaB 4 Na 24. Select the statement that correctly describes this reaction. C 3 C- C 2 Cl 2 (A) Enantiomers are formed in equal amounts. (B) Diasteromers are obtained in equal amounts. (C) Diasteromers are obtained in unequal amounts. (D) An achiral compound is the major product. 25. Compound X, C 7 12, is optically active. ydrogenation of compound X produces a pure chiral product. Select the compound that best fits the experimental data. 3 C C 3 3 C C 3 3 C C 3 3 C C 3 Correct Answer: D
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