HOWEVER please produce a poster no smaller than 11 x 17 inches which represents the contents of your presentation for submission on June 8th:

Transcription

1 Notice to CH 242 Students This represents the new material that will be ~50% of the Cumulative final on Tuesday June 8th. The other review material will be similar to previous exams/practice exams homework problems. The exam will only cover through chapter 14. The term assignement will be handed in in written form on the final exam day; it is unlikely we will have time for presentation HWEVER please produce a poster no smaller than 11 x 17 inches which represents the contents of your presentation for submission on June 8th: this can be similar to your written paper but in a single panel format suitable for viewing from a distance (font no smaller than about 18pt) You could print out PowerPoint slides if you have prepared them for the presentation or use other materials. This poster will be in addition to your written paper and will be graded as your presentation. In addition a class review will be available online that will add 5% to your class point total, please check back to the WEB site and fill in this review before the end of next week to get credit. Enter your name (NT you ID#) when completing the review, it will not be traced, your opinions are anonymous, and appreciated.

2 CH242 True/False Indicate whether the sentence or statement is true or false. 1. The highest m/z value corresponds to the molecular ion peak 2. A mass spectrometer can detect either cationic and radical species 3. arene oxides are important biological breakdown products of aromatic compounds 4. The base peak is always the highest peak 5. The β-spin state has higher energy than the α-spin state 6. The nucleii in an NMR experiment are in resonance with the magnetic field 7. Higher Rf frequencies and stronger magnetic fields give NMR spectrometers with better sensitivity 8. A Fourier Transform yields frequency based data from time based data 9. In an NMR experiment, the effective magnetic field is always smaller than the applied magnetic field 10. Diethyl ether has 4 groups of equivalent protons 11. The 1 H NMR peak for a phenolic proton would be relatively broad 12. In 1 H NMR deutrium is invisible 13. You could take an MRI of a mummy if it wasn't completely dry 14. The addition of a small amount of acid would simplify the 1 H NMR spectrum of an alcohol 15. Equivalent protons can sometimes be made non-equivalent at lower temperatures 16. Proton coupling can only occur through three σ-bonds 17. Proton coupling can occur through four bonds if one is a double or triple bond. Multiple Choice Identify the letter of the choice that best completes the statement or answers the question. 18. The Heck, Stille and Suzuki and reaction have in common a. palladium tetra(triphenylphosphine) b. the coupling of two carbon compounds c. their similarity to the Gilman reaction 19. The reaction of an arene oxide with the hydroxide anion gives a. an addition product b. a diol c. an enone intermediate

3 20. A crown ether could a. solvate a cation b. form an inclusion compound c. be used as a phase transfer catalyst 21. a thiol can be a. dimerized by oxidation b. bridged by a mercuric ion c. deprotonated and used as a nucleophile in an S N 2 reaction 22. Using a copper bowl to whip your egg whites gives a nice stiff merangue because? a. acetic acid b. butyric acid c. caprioc acid d. formic acid 23. The base peak and molecular ion peaks are what molecules, respectively? a. + CH 3 CH 2 CH 3 and CH3 CH 2 CH 2 CH 2 CH 3 b. + CH 3 CH 2 CH 2 CH 2 CH 3 and CH3 CH 2 CH 3 c. + + CH 3 CH 2 CH 3 and CH3 CH 2 CH 2 CH 2 CH 3 d. + + CH 3 CH 2 CH 2 CH 2 CH 3 and CH3 CH 2 CH The peaks at 122 and 124 represent what? a. the molecular ion and the diprotonated molecular ion b. the products of α cleavage

4 c. the products of heterolytic cleavage d. a reflection of the isotopic distribution of bromine atoms in nature 25. The molecular ion peak of an alcohol is a. The base peak because its so stable b. usually a doublet c. very small because its so unstable d. None of these responses are correct. 26. The mass spectrum of an unknown compound has a molecular ion peak with relative intensity of 43.27% and the M + 1 peak with a relative intensity of 3.81% How many carbons are in the compound? a. 4 b. 6 c. 8 d In an NMR experiment higher δ values correspond to a. electron poor protons b. deshielded protons c. higher frequency resonance 28. In an NMR experiment lower δ values correspond to a. electron rich protons b. shielded protons c. lower frequency resonance 29. CH 3 CH 2 CH 2 N 2 A B C The order of 1 H δ values from highest to lowest for this compound would be: a. A > B > C b. C > B > A c. C > A > B d. C > B = A 30. Good examples of diamagnetic anisotropy include a. the high δ values of benzyl protons b. the high δ values of vinylic protons c. none of these d. both a and b 31. 1,1-dicloroethane would give what 1 H NMR spectrum from left to right? a. a doublet and a singlet b. a doublet and a triplet c. a quartet and a doublet d. a quartet and a triplet 32. The 1 H NMR spectrum of 1,2-dichloroethane gives only one singlet because a. equivalent protons don't couple b. the two groups of equivalent protons are coupled

5 c. it has two groups of equivalent protons d. none are correct 33. In an 1 H NMR experiment, a group of equivalent protons that are adjacent to a methine carbon would give rise to a a. singlet b. doublet c. triplet d. quartet 34. Nitrobenzene would give what 1 H NMR spectrum, from left to right? a. doublet, triplet, quartet b. quartet, doublet, triplet c. triplet, quartet, doublet d. doublet, quartet, triplet 35. ClCH=CHCH This compound gives an 1H NMR spectrum with doublets with a J value of ~9Hz a. it is a cis compound b. it is a trans compound c. it is a meso compound d. there is no way to tell Short Answer 36. How would the following synthesis be carried out? 37. How would be the product of the following reaction? 1. CH 3 CH 2 MgBr 2. H How would be the product of the following reaction? Br 1. Mg H 3 + CH How would the following product be made? S C H What would the product of the following reaction be?

6 I + (CH 3 CH 2 CH 2 ) 2 CuLi

7 CH242 Answer Section TRUE/FALSE 1. T 2. F 3. T 4. T 5. T 6. F 7. T 8. T 9. T 10. F 11. T 12. T 13. T 14. T 15. T 16. F 17. T MULTIPLE CHICE 18. D 19. D 20. D 21. D 22. D 23. C 24. D 25. C 26. C 27. D 28. D 29. B 30. D 31. C 32. A 33. B 34. A

8 35. A SHRT ANSWER H H + heat CH 3 CH page CH 3 CH 2 MgBr H CH 3 2. H see page 468 Br MgBr Mg Mg 2+ Br - H H 39. SH H - S S Br CH 2 C Br - H 2 see page 465 problem # see page 470