name ______________________________ Page 1 of 6 1-10. Multiple Choice. Provide the best answer for each question. There is only one answer for each question. (3 pts each, 30 pts total) 1. Which of the following is NOT a feasible synthesis of tert-butyl methyl ether? NaH, THF a) (CH3)3COH + CH3I NaH, THF b) (CH3)3C-Br + CH3OH 1) Hg(OAc)2 c) (CH3)2C=CH2 + CH3OH 2) NaBH4 d) a, b, and c are all feasible methods for the preparation of t-butyl methyl ether 2. From the pKa's of the following substituted benzoic acids, which substituted benzene is predicted to be MOST reactive toward electrophilic aromatic substitution O R= -H pKa= 4.20 R= -CH pKa= 4.40 OH 3 R= -OCH3 pKa= 4.50 R R= -NO2 pKa= 3.42 a) CH3 b) OCH3 c) NO2 d) There is no relationship between the pKa of substituted benzoic acids and the reactivity of substituted benzenes in electrophilic aromatic substitutuion 3. Which of the following structures would be consistent with a carbonyl stretch at 1685 cm-1 in the infrared spectra? a) O b) O c) O d) O H 4. Which of the following would NOT be a product from the reaction of methyl phenyl ether with HI? a) OH b) I c) d) H C-I Products a, b, and c 3 will all be produced in the reaction 5. The reaction below is an equilibrium. Which of the following methods will drive the reaction to products? O OCH3 + 2 CH3OH + H2O OCH3 a) Use a large excess of methanol b) Remove the water produced in the reaction as it is formed c) Add a catalyst d) a and b only name ______________________________ Page 2 of 6 6. Which of the following best describes the mechanism of the Williamson ether synthesis? a) SN1 reaction b) SN2 reaction c) E2 reaction d) nucleophilic acyl substitution 7. Which of the following compounds is predicted to have the lowest pKa? a) O b) O c) O d) O F Cl OH F OH OH OH 8. Which of the following is NOT an ylide? _ a) + _ b) + c) + O d) Ph P CH H3C S CH2 3 2 H3N _ a, b, and c are all ylides CH3 O 9. Which of the following does NOT normally react with an amine to give an amide? a) carboxylic acid b) acid chloride c) anhydride d) ester 10. Which of the following reactions or reaction sequences is NOT a feasible synthesis of benzoic acid? Br 1) Mg(0), ether a) 2) CO2 + 3) H3O 1) NaCN Br + b) 2) H3O O c) H Ag2O, NH4OH d) a, b, and c are all feasible methods for the preparation of benzoic acid name ______________________________ Page 3 of 6 11. Provide a stepwise mechanism for the reaction below. (14 pts) O CH3 HCl N CH + H3C-NH2 + H2O 3 CH3 12. Provide a stepwise mechanism for the reaction of benzoyl chloride with methanol to give methyl benzoate. (10 pts) O O Cl + CH3OH + HCl OCH3 name ______________________________ Page 4 of 6 13. From the list below, provide the best reagents to complete the following reactions. (3 pts each, 9 pts total) A. POCl3, pyridine H. 1) (CH3)2CuLi, THF 2) H3O+ B. DIBAH, toluene I. Ph3P-CH3 I-, nBuLi C. H2NNH2, KOH J. m-chloroperoxybenzoic acid (mCPBA) D. 1. LiAlH4 2. H3O+ K. PCC E. H2, Pd/C L. KMnO4 F. 1. BH3 2. H3O+ M. CrO3, H3O+ G. SOCl2 N. NH2OH, H+ CH3 OH O CH3 O O OH OH O N 2 O2N 14. Each of the following transformations require two steps. From the same list of reagents as Question 13, give the required reagents over the arrows and the intermediate in the box. (18 pts) OH CH3 CH3 O O OCH3 O O OH CH3 name ______________________________ Page 5 of 6 15. Give the major product for the following reactions (9 pts). O 250 °C Cu Li O 1) 2 + 2) H3O O 1) CH3MgBr + 2) H3O 16. Provide a structure consistent with the following spectroscopic data. (10 pts) Formula: C10H12O2 IR: 1690 cm-1 13C NMR: d 200, 158, 130, 128, 114, 65, 32, 10 1H NMR: d 7.80 d, J= 9.0, 2H 7.10 d, J= 9.0, 2H 3.90 s, 3H 2.50 q, J= 6.0, 2H 1.20 t, J= 6.0, 3H name ______________________________ Page 6 of 6 ____________________________________________________________________________________ Problem 1-10:________ (30 pts) 14:________ (18 pts) 11:________ (14 pts) 15:________ (9 pts) 12:________ (10 pts) 16:________ (10 pts) 13:________ (9 pts) Total out of 100: _________.