1. Complete the template below to show the stereochemistry of (3R,4R) 3-chloro-4,5,5- trimethyl-hexane-1,4-diol.
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1 Chemistry 51 Exam 1, Fall 2004 This is a closed book exam. The exam lasts 50 minutes. All answers must appear on the answer sheet. Only the answer sheet will be collected. Put your name on the answer sheet now. When the exam is over you must hand your answer sheet in promptly or a penalty may be incurred. ============================================================== 1. Complete the template below to show the stereochemistry of (3R,4R) 3-chloro-4,5,5- trimethyl-hexane-1,4-diol. Cl 2. a) Which of the structures below represent (2R,3R) butane-2,3-diol? Answer by letter. b) Which represent enantiomers of (2R,3R) butane-2,3-diol? Answer by letter. c) Which represent diastereomers of (2R,3R) butane-2,3-diol? Answer by letter. O O O O O O 3 C O 3 C A B C D 3. a) Which of the following is expected to be the strongest acid? b) Which is expected to be the strongest base? a. trifluoroacetic acid CF 3 CO 2 b. acetic acid c. cyclohexane d. trimethylamine, ( ) 3 N O
2 4. 2,3,4-trimethyl-pentane is monochlorinated and the product mixture carefully distilled into various fractions. Characterize the product mixture by filling in the boxes. Put final answers on answer sheet. ow many fractions are optically active? ow many fractions consist of a single compound? ow many fractions consist of racemic material? 5. A sample of 2-bromobutane is 40% optically pure R stereoisomer and the observed specific rotation is -40 degrees. The sample is reacted with hydroxide ion to yield 2- butanol having an observed specific rotation was -5.0 degrees). Pure, (R) 2-butanol has a specific rotation of 50.0 degrees. What fraction of the reaction has occurred with inversion of configuration (as opposed to racemization of configuration)?
3 ============================================================== For the following reactions give the missing reactants or products. Show the stereochemistry. Write "NR" if there is no reaction. Put answers on the answer sheet. ============================================================== 6. O P 3 Mg OD 7. 3 C TsCl acetic acid O S N 1 ester 8. excess NaCN CN C 2 5 S N 2 CN Complete the template
4 9. Using alcohols having five or fewer carbons and any inorganic reagents provide an efficient synthesis of the compound below. C 2 5 C 2 C( ) When optically active 2-butyl tosylate is reacted with ethanol the resulting ether has a small specific rotation. In contrast, if the ethanol contains sodium ethoxide then the ether has a much larger specific rotation. Explain briefly. 11. For the S N 2 reaction given below a) Sketch the transition state. b) What will happen to the rate of reaction as the polarity of the solvent is increased. c) Why? N 2 + I 2 N( ) 2 + I 12. For the reaction of ethane and bromine to yield bromoethane sketch the transition state for the rate determining (chain) step. Be sure to show relative bond strengths. 13. Both trans cinnamic acid and urea have melting points of 133 degrees. a) Characterize the melting of a mixture of 5% trans cinnamic acid and 95% urea. b) An unknown compound is either trans cinnamic acid or urea. You have available genuine samples of both trans cinnamic acid and urea. ow do you determine the identity of the unknown?
5 14. a) Draw a resonance structure for the carbocation below wherein the octet rule is obeyed for each atom. Cl b) Draw a hyperconjugation resonance structure for the 2-propyl carbocation showing how the methyl groups stabilize the positive center. 3 C 2-propyl carbocation 15) An unknown compound, X, has the formula C 9 14 and is optically inactive. Complete hydrogenation yields two pure optically inactive compounds (not a racemic mixture), A and B, each having the formula C a) Suggest a structure for the compound X. (There are several answers possible answers.) b) It is further found that compound A forms five monochloroderivatives. Refine your choice for the structure of X.
6 Answer Sheet Your name Recitation Instructor: owell Kripkowska Mollica Silbering Shakya All answers must appear on answer sheet. 1 (8) 2(6) a 3(6) a Cl b c b 4(9) ow many fractions are optically active? ow many fractions consist of a single compound? ow many fractions consist of racemic material? 5(6) 6(7) 7(7) 8(7)
7 Your name 9 (7) 10(7) 11 (6) a b c 12 (6) 13 (6) a b 14 (6) a b 15 (6) a b
1. Name the following compound. Use the IUPAC system and include the stereochemical designations.
Chemistry 51 Exam 1, Summer 2004 This is a closed book exam. The exam lasts 100 minutes. All answers must appear on the answer sheet. Only the answer sheet will be collected. Put your name on the answer
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