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1. Determine the number of peaks you would expect to see from the following molecule IIII. a. in a 1H NMR spectrum (do not count splitting patterns). Answer: b. in a proton decoupled 13C NMR spectrum. Answer: 2. Determine the structure of this alcohol with the molecular formula C5H12O from its 1H NMR spectrum. 1H NMR 6H 1.8 1.7 1.6 1.5 1.4 2 H (CH3)4Si 2 H 1 H 1 H 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 300-MHz 1H NMR spectrum ppm (8) 3. The 13C spectrum of a compound with the molecular formula of C5H10O shows peaks at the following locations. The type of carbon was revealed by DEPT spectra. Draw the structure of one of the possible isomers. 8=17.6 (CH3), 25.4 (CH3), 58.8 (CH2), 125.7 (CH), 133.7 ppm (Cq) 4. Draw the structure of (Z)-3,7-dimethyl-3-octene 5. Decide which of the following statements are correct for compound A, compound B, both, or neither of them (write "A", "B", "both", or "neither" on the line given): A B H3C H H3C CH3 H CH3 H H a. This compound is more stable. b. This compound is slightly polar. C. This compound would release more energy upon hydrogenation. 6. 3-Hexanol is oxidized to the ketone. Where would you expect to see major changes in the IR spectrum over the course of the reaction? Give approximate wavenumbers and peak shapes of one appearing and one disappearing peak. 7. Determine the structure of the alkane producing the following mass spectrum. Draw the fragments causing m/z = 43 and m/z = 85 (include charges and unpaired electrons) and explain the intensities of these peaks in the mass spectrum. 100 43 90 80 70 60 50 40 85 57 30 20 29 10 71 100 10 20 30 40 50 60 70 80 90 100 110 m/z 8. a. Draw the major organic product of this E2 reaction. H H KOH EtOH/heat Br b. Draw the conformer out of which this E2 reaction will occur in Newman projection. C. What would the product look like if we would let this haloalkane react with KOtBu instead of KOH? 9. Draw the mechanism of the following reaction leading to the major organic product. HBr H Propose reagents to perform the following OH 10. a. OH OH b. OH OH OH C. + OCH OCH3 Br d. 11. a. Show the mechanism for the conversion of A into B (and its enantiomer). CI Cl2 HO OH A B b. How could A be converted into C? Show the mechanism. OH CI C 12. Indicate how this reaction could be performed with good yield. Show the product of the first step. Only one enantiomer of the product is shown. Show the enantiomer of the first step that leads to this enantiomer in the product.

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