Organic Chem II Spring 2008 Exam 3

Organic Chem II Spring 2008 Exam 3 - OM - PR EME D41 1.C P...

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Unformatted text preview: OM - PR EME D41 1.C P 1.C OM CHM 202- Organic Chemistry II - PR EME D41 Exam 3 Key. Answers on last page. - PR EME D41 1.C OM 1. An alkene adds hydrogen in the presence of a catalyst to give 3,4dimethylhexane. Ozonolysis of the alkene followed by treatment with zinc and water gives a single organic product. The structure of the alkene is: b. e. D41 d. - PR EME c. 1.C OM a. c. III d. IV - PR EME D4 b. II e. V COM - PR EME D4 11. COM a. I 11. COM 2. Hydroxylation of cis-2-butene with cold alkaline (basic) KMnO4 yields 11. COM - PR EM ED4 11. COM - PR EM ED4 11. 3. The aldol reaction of cyclohexanone produces which of these selfcondensation products? a.I b.II c.III d.IV e.V 11. COM - PR EM ED4 4. Treatment of 3-heptanone with sodium borohydride followed by H3O+ yields two organic products while treatment of 4-heptanone with the same sequence of reagents yields one organic product. Which statement best explains this observation? is more reactive less susceptible to reductive transformation has two different leaving groups whereas 4-heptanone is less susceptible to oxidative transformation above - PR EM ED4 11. COM - PR EM ED4 a. 3-heptanone b. 4-heptanone c. 3-heptanone only has one d. 4-heptanone e. none of the MPRE M ED4 11. COM 5. The product, X, of the following reaction sequence, would be: b. c. d. PRE MED 411 .CO a. 1 e. OM 1.C D41 - PR EME D41 1.C OM 6. The following generalized reaction, would give which product? 1.C b. c. d. - PR EME D41 a. OM - PR EME e. - PR EME D41 1.C OM 7. What would be the product, L, of the following reaction? Assume the Ni catalyst in the second step functions the same as Pd on C. c. III d. IV COM b. II e. V COM - PR EME D4 11. a. I c. III COM b. II d. IV e. V - PR EM ED4 11. a. I - PR EME D4 11. 8. What is the chief product of the Hofmann elimination reaction applied to the compound shown at far right? c. III COM b. II 11. a. I - PR EM ED4 11. COM 9. What is(are) the product(s) of the Dieckmann condensation of this diester (in other words, treating this with sodium ethoxide in ethanol yields…) e. I, II, III - PR EM ED4 d. I, II - PR EM ED4 11. COM 10. A dilute solution of cyclohexanone in D2O/DCl is shown to exchange all its α-hydrogens for deuterium to form 2,2,5,5- tetradeuteriocyclohexanone. Which best explains this outcome under these conditions? enolate formation is reversible enolate formation is irreversible enol formation is reversible enol formation is irreversible the kinetic isotope effect governs the product outcome - PR EM ED4 11. COM a. b. c. d. e. 11. What product is finally formed when MPRE M ED4 11. COM the initial compound formed from cyclohexanone and pyrrolidine is mixed with allyl chloride (ClCH2CHCH2) and that product is hydrolyzed in HCl/H2O? b. II c. III d. IV e. V PRE MED 411 .CO a. I 2 OM 1.C D41 - PR EME 1. O3 OH 2. H2O2 C omp oun d A 1.C OM 1 only 1, 2 2, 3 1, 3 1, 2, 3 KM nO 4, OH -, ∆ - PR EME D41 2. OM a. b. c. d. e. O 1. - PR EME D41 1.C OM 12. Identify all possible valid routes to compound A from the choices below. O D41 1.C 3. E tO - PR EME 1. Na OE t 2. Br(C H 2)5B r O 3. Na OE t 4. HC l, H 2O , ∆ OE t COM 13. Indicate the product of the following: O - PR EME D4 a. O 2. Cl 3. H Cl, H2O H H O O O O d. O O O H O O H O e. N one of t he abo ve COM H c. O - PR EME D4 11. O 4. OH -, b. COM O 11. 1. py rrolid ine, c at . H + - PR EM ED4 11. 14. Identify the proper reagents/conditions for the following transformation. a. O O b. 2. K+ - O tBu c. O , Na O H, ∆ 3. COM ? 1. H+ , Br2 O 1 . LD A 3 . H 2O , HC l, ∆ 2. 11. C uL i d. 1. H+ , p yrro lid in e 2. c yclo he xan on e 3. H+ , ∆ COM - PR EM ED4 e. No ne o f t he ab ove - PR EM ED4 11. 15. Which would NOT form essentially one Claisen condensation product when one compound is added slowly to the mixture of the other in NaOEt? a. O O Et COM 11. ED4 - PR EM O + O Et OE t O O O O + Ph OE t OE t ED4 11. COM + Ph O O O OH O a. O O b. d. c. O O O e. O O O O 411 MED PRE O OE t .CO MPRE M O OEt d. O EtO 16. H OE t O e. OE t + OE t 11. ED4 - PR EM c. O b. + COM Ph O 3 OM 1.C D41 - PR EME 1.C b. + O OH O D41 O- OM N N N N 1.C O e. d. N - PR EME H N c. D41 a. Other than the two reactants shown, OM 17. Identify the major product. there are no other additives. OM - PR EME 18. Which would be the preferred ylide for making A via a Wittig reaction? (Assume you would pair this with the appropriate partner molecule). 1.C D41 - PR EME 3. H 2C P(P h)3 P(P h) 3 4. COM 1 2 3 4 2 or 3 equally preferred P (Ph )3 2. - PR EME D4 11. a. b. c. d. e. P(P h)3 1. A. COM 19. An alkene with molecular formula C8H14 is treated with ozone and then zinc and water. The product isolated from these reactions is: What is the structure of the alkene? c. d. 11. a. O e. - PR EME D4 b. H 11. COM O - PR EM ED4 20. Which would form a Claisen condensation product when treated with NaOEt followed by acidfication? O O c. O Et d. O O Et ED4 O Et e. O Et 11. Ph COM b. a. O Et O - PR EM O COM 21. Indicate the major product. 11. O OH -, ∆ O b. a. O O d. c. e. No ne of t he abov e COM - PR EM ED4 O O 11. O ED4 22. Which pair of compounds/conditions is best suited to making the following? ? H2 O a. O ED4 11. COM - PR EM + - PR EM COM 11. ED4 O O b. O O H H + H H ad d s l o wl y t o + X S i n Na O H ad d s l o wl y t o X S i n Na O H c. O MPRE M .CO 411 MED PRE O H + O O H + a d d s l o w l y to e. No ne of the ab ov e d. O X S in N a OH 4 a d d s l o w l y to X S i n N aO H OM 1.C D41 - PR EME D41 1.C OM 23. Which organic reagents would you need to make 2-ethylpentanoic acid from diethyl malonate? O 3-bromohexane and sodium ethoxide bromoethane, 1-bromopropane, sodium ethoxide 3-bromopentane and sodium ethoxide bromoethane, 2-bromopropane, sodium ethoxide 2-bromopentane and sodium ethoxide - PR EME a. b. c. d. e. O OM EtO OEt - PR EME D41 1.C d iet h y l mal o n ate D41 1.C OM 24. Which pair of compounds will produce the Robinson annulation product shown. - PR EME O a. - PR EME D4 11. COM O b. O O O d. e. No ne of the a bo ve O O O - PR EME D4 11. O O c. COM O O - PR EM ED4 11. COM 25. 22. Which of the following would provide the best synthesis of 3,5-dimethyl-2-hexanone starting from ethyl acetoacetate? A) 1. NaOC2H5 + CH3I; 2. NaOC2H5 + (CH 3)3CCH2Br; 3. H3O+ + heat B) 1. NaOC2H5 + (CH3)3CBr; 2. NaOC2H 5 + CH3I; 3. H3O+ + heat C) 1. NaOC2H5 + (CH3)2CHCH2Br; 2. NaOC 2H5 + CH 3I; 3. H3O+ + heat D) 1. NaOC2H5 + (CH3)2CHCH2CHBrCH 3; 2. H3O+ + heat E) 1. NaOC2H5 + CH3I; 2. NaOC2H5 + (CH 3)2CHBr; 3. H3O+ + heat 11. ED4 3.b 15.a - PR EM 2.b 14.b 4.e 16.c 5.e 17.e 6.a 18.c 7.e 19.d PRE MED 411 .CO MPRE M ED4 11. COM - PR EM ED4 11. COM - PR EM ED4 11. COM 1.b 13.a 25.c 5 8.a 20.e 9.d 21.e 10.c 22.c 11.b 23.b O E tO et hyl ace toa ce tate COM - PR EM ED4 11. COM O 12.d 24.c ...
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This note was uploaded on 10/09/2011 for the course CHM 202H/F taught by Professor Heller during the Fall '11 term at FIU.

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