Organic Chemistry II CHM 2211 Sample Exam 2 Answer Key
Transcription
Organic Chemistry II CHM 2211 Sample Exam 2 Answer Key
Organic Chemistry II CHM 2211 Sample Exam 2 Answer Key I. Write Structures for the compounds named below: (12 points) CHO O H2N C H3C NH2 CH3 _______________________ Acetone _________________________ Hydrazine ________________________ Cyclohexane carbaldehyde NH II. H3C O CH2 CH2 CH2 C CH2 CH C CH3CH2P(C6H5)3 _______________________ An ethyl ylide of triphenylphosphine O CH3 _________________________ Any imine ________________________ 3-Oxo-6-phenylhexanal Name the compounds whose structure is shown below: (6 points) O O CH3 C O CH3 CH3 CH3 CH CH2 CH 2-methylcyclopentanone _______________________ OH 3-methylbutanal _________________________ O C CH3 CH CH2 C CH3 4-hydroxy-2-pentanone _______________________ CH3 O O H acetophenone ________________________ H formaldehyde (methanal) _________________________ O CH3 CH CH2 CH2 CH 4-methoxypentanal ________________________ III. Fill in the Blanks (13 points) 1. Why does the carbonyl carbon have a partial positive charge? Because of the electron withdrawing nature of the oxygen 2. When an aldehyde is considered as a group, it is called carbaldehyde group. When a ketone cannot be named as an -one, it is named as an oxo- group. 3. An oxidizing agent that can oxidize an alcohol to an aldehyde without going all the way to an acid is (write the whole name) pyridinium chlorochromate (PCC). 4. CrO3 in H2SO4 is called Jones’ Reagent while R2LiCu is called Gilman’s reagent. 5. A positive Tollen’s test for aldehydes is indicated by the formation of a silver mirror on the test tube. 6. Two important types of diols are geminal and vicinal. Which is the least stable? Geminal diols are unstable. 7. The Clemmenson reduction will reduce a(n) ketone or aldehyde to a(n) alkane (-CH2). 8. Which would be easier to identify using IR spectroscopy, an ether or a ketone? ketone 9. Alcohols are capable of hydrogen bonding with water but aldehydes are not. (T/F) False 10. Which would be easier to oxidize with Jones' Reagent, a ketone or an aldehyde? aldehyde IV. Write a multi step reaction mechanism for the reaction of phenylmagnesium bromide ( MgBr) with acetone to form an alcohol. Indicate intermediates that may or may not be isolated. Use curved arrows to indicate electron attack and show charges and intermediates. (9 points) O C H H3C CH3 MgBr OH2 O C H3C CH3 MgBr OH H3C V. 1. CH3 H2O Complete the following reaction equations by filling in the missing information: (40 points) HCN CH3CH2OH H2SO4 CN - Cl SOCl2 CH3 CH2 C O H2O, heat CH3 CH3 O MnO4- , OH- 2. heat O O 3. AlBr3 + t-But-Br CH3 4. OH tert-butylbenzene Na2Cr2O7 H MnO4 , OH No Reaction (no benzylic H) No Reaction (tertiary alcohol) / H2O O 5. O CH2 AlCl3 + H3C Cl 6. H3C O CH2 CH2 LiAlH(OtBu)3 O CH3 CH2 CH2 CH Cl CH3O O OCH3 H 7. + 2 CH3OH O OH H3O 8. C + H3C HCl C H3C CH3 CH3 Cl 9. O Na2CrO7 CH2 OH C OH CH3 H3O HC CH3 O CH3 10. HC + HCN CH3 CH2 CH CH2 C CH3 CH3 CH2 1. LiAlH4 CH2 2. H3O HC CH2 OH CH2 O 11. CH2 HC OH CN CH3 CH3 + CH3-NH-CH 3 NH2 N CH3 12. NH OH CH2O + NH3 C H2O 13. CH 3CH 2P( H CH 2O H CH3CH=CH2 OH 14. O + N2H4 O CH2 OH 15. PCC C H 16. 1. DIBAlH CH3CH2CHO CH3CH2COOH 2. H3O O 17. CH3 CH CH C O CH3 O 1. LiAlH4 2. H3O OH 18. 1. NaBH4 2. H3O CH3CH=CH-CH2-OH + HO-CH3 O O 19. + HCN O H3C 20. C NC O Ag2O, NH4OH H + Ag (mirror) OH VI. Multiple Choice (Circle the letter of the best answer) (20 points) 1. Below might be the spectrum of a carboxylic acid. Which two features make this likely? a. b. c. d. 2. Which compound will reduce C=O but not C=C (at least not much)? a. b. c. d. e. 3. Jones’ Reagent PCC LiAlH4 NaBH4 Chromic Acid Which of these is not an oxidizing agent? a. b. c. d. e. 4. The broad peak above 3000 cm-1 and the sharp peak at 1710 cm-1 The peaks at 1240 and 1090 cm-1 The sharp peak at 3000 cm-1 and the sharp peak at 1240 cm-1 This is probably not the spectrum of a carboxylic acid. PCC DIBAH Na2Cr2O7 in H2SO4 Jones’ Reagent Hypochlorite Alkoxymercuration followed by borohydride reduction would be used to produce a. b. c. d. e. an alcohol from an alkene. an aldehyde from alcohol. an acid from and alkyne. an ether from an alkene. an alkene from an aryl halide. 5. Which of the following is not a common reaction of aldehydes? a. b. c. d. e. 6. When CN-1 is reacted with carbonyl compounds followed by protonation of the oxygen, what do we call the products? a. b. c. d. e. 7. make the compound soluble. oxidize the compound. confirm the identity of a compound by the MP of the derivative. make the compound colored. produce a Grignard reagent for further reaction. How would you easily tell the difference between a proton NMR (1HNMR) and a carbon (13CNMR) spectrum? a. b. c. d. e. 10. Alcohols Aldehydes Ketones C=O Methyl on a carbonyl 2,4 DNP derivatives of carbonyl compounds are often made to a. b. c. d. e. 9. Cyanohydrins Nitriles Ketones Imines Enamines In proton NMR, which compound or groups will show a characteristic peak near 10 ppm? a. b. c. d. e. 8. Nucleophilic acyl addition Nucleophilic acyl substitution alpha Substitution Carbonyl condensation Reduction to a ketone by looking at the size of the peaks by looking at the location of the peaks by looking at the horizontal scale by looking at peak splitting by looking for the internal standard peak Hemiacetals and acetals are often found in a. b. c. d. e. carbohydrates. proteins. fats. oils. DNA.