Unformatted text preview: name ______________________________ Page 1 of 6 Multiple Choice. Choose the best answer for the following questions. (10 questions, 40 pts) 1. Calculate the degrees of unsaturation for a molecule with the molecular formula C9H10FNO3 (a) (b) (c) (d) (e) 2. 0 3 4 5 6 A reaction A ! B occurs in a single step and has a "G of 50 KJ/mol. According to the Hammond Postulate, the structure of the transition state for this reaction would most resemble: (a) (b) (c) (d) (e) the reactant, A the product, B it would be an equal hybrid of A and B the reaction intermediate there is no way to predict the structure of a transition state 3. Increased substitution stabilizes an alkene due to hyperconjugation. Hyperconjugation involves a bonding interaction between an adjacent C-H #-orbital with... (a) (b) (c) (d) (e) the alkene #-orbital the alkene #*-orbital the alkene $-orbital the alkene $*-orbital an unhybridized p-orbital 4. Which of the following is (E)-2-chloro-3-methyl-3-hexene?
(a) (b) (c) Cl CH3 (d) Cl Cl Cl (e) Cl 5. Which of the following would be the product of the reaction shown below?
H2 , Pd/C (a) H (b) H (c) OH (d) H (e) O H H H OH O 6. name ______________________________ Page 2 of 6 The pKa of acetylene is 25. Which of the following bases could be used to generate the acetylide anion? (a) (b) (c) (d) (e) H3C(pKa of CH4 = 60) H3N(pKa of NH3 = 35) - (pKa of CH OH = 16) CH3O 3 all of the above a and b only 7. Which of the following reagents must be used with HBr to convert 1-hexene to 1-bromohexane? (a) (b) (c) (d) (e) HSO3NaBH4 ROOR Pd/C no other reagent is necessary. 8. Which of the following statements concerning a carbocation is not true? (a) (b) (c) (d) (e) the hybridization is sp2. the geometry is trigonal planar. they are stabilized by hyperconjugation. they cannot be observed, isolated or trapped. statements (a)-(d) are all true. 9. Which of the following molecules is in the highest oxidation states? (a) (b) (c) (d) (e) an carboxylic acid. an alcohol. an aldehyde. an alkane. all are in the same oxidation state. 10. An organic molecule has a molecular formula of C10H13N. Upon hydrogenation of this molecule with Pd/C, it reacts with 2 mol equivalents of H2. Hydrogenation with Lindlar's catalysts gives no reaction. Which of the following structures is constant with this information?
(a) N CH3 (d) H3C N CH3 (e) all structures are constant with the information given (b) C (c) N C N name ______________________________ Page 3 of 6 11. Draw a complete mechanism for the following reaction. (8 pts)
CH3 HCl Cl CH3 H-Cl CH3 + 2 carbocation H + Cl _ 1,2-methyl shift Cl _ CH3 H + Cl 3 carbocation 12. Give the product and complete mechanism for the reaction of Br2 with cyclopentene in H2O. Your mechanism should clearly show any stereochemical preference. (8 pts)
OH2 Br Br Blocks bottom face H H O H H O H Br OH + H-Br Br Br H H Br+ H Br name ______________________________ Page 4 of 6 13. Given the alkene or alkyne reactant needed to obtained the product via the reaction shown below. (12 pts)
H OH CH2 1) BH3 2) H2O2, NaOH, H2O anti-Markovnikov hydration KMnO4 O O OH H H CH2I2, Zn(Cu) H H 14. Give the reagent(s) required to complete the following reactions. (12 pts)
HgSO4, H3O+ O H-Br (Z)-3-Bromo-3-hexene Br Br2, CCl4 CH3 H Br name ______________________________ Page 5 of 6 15. Give the product for each of the following reactions. Draw the product in its most stable chair conformation. (12 pts)
H H2, Pd/C H CH3 OH NBS, DMSO, H2O H Br C(CH3)3 CH3 1) OsO4 2) NaHSO3 H H OH OH 16. Fill in the required intermediate products and reagents necessary to complete the following synthesis. (8 pts) NaNH2 or KOH Br Br NaNH2, 1-bromopropane Li, NH3 CH2I2, Zn(Cu) H H name ______________________________ Page 6 of 6 ____________________________________________________________________________________ Problem 1-10:________ 11:________ 12:________ 13:________ 14:________ 15:________ 16:________ (40 pts) (8 pts) (8 pts) (12 pts) (12 pts) (12 pts) (8 pts) Total out of 100: _________ ...
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