Exam 3 UTA Review Sheet 1. Provide a structure that fits the following descriptions: a, A.compound with enantiomeric hydrogens (identify the specific hydrogens) b. A reducing agent that tus carbonyl groups to alcohols c. Adi-alkyl cuprate d. An epoxide . A reagent that can make an alcohol functional group into a bromide functional group 2. There are two possible pathways to make the ether shown below. Which of the pathways will have a higher yield of the product and why? OOO Pathway Pathoay3. Show the mechanism for the following reaction: es oud serail El er 4, "H-NMR and "C-NMR are run on the following compound. Indicate how many H signals are likely to be seen, and how many C signals will be seen. Also provide a rough sketch of the H NMR. Cl 5. A student is running a sample through electrospray ionization (ESI) in the lab and finds that its molecular weight appears to be 113.23, and he uses that to get an estimate of the molecular formula, His lab partner says that they should instead use the molecular weight of 90.23 to get the molecular formula, Which student is correct?6. Agtee or disagree with the following statements and explain your answer: a. The two hydrogens below will couple with each other in the following molecule. (Note: for this molecule, we only care about the interactions between the 2 indicated hydrogens, not the other implicit hydrogens). OH b. Fragmentation is not a major concern when looking at chemical ionization for mass spectroscopy. In the presence of heat, Cl can displace sulfonate groups. 4. The following reaction is plausible:+ CHI ——_. co OMe Epoxides undergoing a ring opening reaction through an SN1-type mechanism will yield OH perfect racemic mixtures (50:50 ratio) Electron-donating groups (EDGs) cause downfield shifts on a "H-NMR spectrum. If we wished to use this in a grignard reaction, it would not yield any unwanted or side products, therefore a protecting group is not needed. Mg — Br7, Draw a reagent that could, in one step, use this reactant to get this product INN ONO 8. Complete the following epoxide reactions (stereochemistry may be important) a MeOH TESO, €. 2,2-dimethyl oxaeyclopropane with NaOMe in Methanol 9. Which reaction is “greener” or in other words, is better from a green chemistry point of view? Justify your answer. (Alkenes aren’t on exam 3, but you should still be able to apply the rules of green chemistry here)1 THE then work- Bg 7 OS TH Hewett “15°C “THF then work ean Te thence 25°C t 10. Given the 'INMRSpectrum below, label which hydrogens on the molecule below correlate to which hydrogens from the spectrum. | vA | 7 Pew 11, How could you confirm, only using IR spectroscopy, that this reaction occurred? ° Perea ee12, Synthesis Practice (using precursors of 4 carbons or less) 13, Draw a stepwise mechanism for a reaction in which an alcohol functional group becomes a halogen funetional group.