NAME___________________________________Final Exam, Organic Chemistry II, CHEM 332Spring 2002, May 17Section 003, Dr. SweetingFull credit on this exam is 200 pointsWith bonuses and extra credit, it is possible to earn 256.I anticipate that I will have completed and submitted the grades for the course by Monday 20May. They should be posted for your perusal within a day. If you wish to learn your final examgrade, you may e-mail me. If you wish to see your final exam, I expect to be in the vicinity of myoffice M-R from May 27 to July 18; stop by then or in the fall.If you are unable to do a problem because of not being able to identify a compound from itsname, you may “purchase” the structure from me for 4 points (except in the nomenclaturequestions).I wish you all success on this exam and in your future studies. Have a great summer!1. Identify the missing reagents in the following scheme. More than one reagent or step may benecessary to accomplish some of the transformations; be sure to make the order of multiplesteps clear. You need not show the inevitable neutralization step for each reaction. Thissequence is McMurry’s problem 20.42. (5 points each, 30 points)OHBrOHOOHHO??????2. Identify the missing reagents in the following scheme. More than one reagent or step may benecessary to accomplish some of the transformations; be sure to make the order of multiplesteps clear. You need not show the inevitable neutralization step for each reaction. (4 pointseach, 40 total) ON+OO??Cl2FeCl3?O?Br2NaOHLiAlH4?NH2CH3ClO???OHone mole Br2??3. Please write the structures of each of these compounds from their IUPAC names (15 points)a) 2-diethylamino-N-(2,6-dimethylphenyl)acetamideb) (R)-2,3-dihydroxypropanal (D-gyceraldehyde)4. Please write IUPAC names for each of the following compounds, including stereochemistrywhere appropriate (25 points): a ) OOb) CH3OOHCH3c) OOH5. Write the currently accepted mechanisms of two or more of the four reactions below. To getfull credit on the exam, you need to earn 30 points on this question. To earn full credit for anymechanism, you must show all the intermediates for which there is some evidence, all protontransfers to and from the organic compounds, and arrows to indicate whether the reaction stepsoccur at equilibrium or not. Extra credit for additional correct answers. a) Base-catalyzed reaction of methyl benzoate with methyl hexanoate. Please identify the bestcatalyst.(10 points)b) Lewis-acid-catalyzed reaction of acetyl chloride with benzene. Please identify the bestcatalyst.(10 points)c) Acid-catalyzed reaction of benzoic acid with 2-propanol to form an ester.(20 points)d) Acid-catalyzed reaction of cyclohexanone with ethane-1,2-diol (ethylene glycol) to form acyclic ketal.(20 points)6. Please explain what the following compounds, reactions or phenomena are, giving anexample (with structure) when possible. (5 points each, 30 total)a) aldopentoseb) polyesterc) diazonium salt d) lipide) neurotransmitterf) polynuclear aromatic compound7. Please outline a synthesis of THREE of the following compounds. Additional solutions willearn additrional credit. (10 points each)a) from organic compounds with fewer carbon atomsOb) (“meth”) from , made aboveNHCH3Oc) from organic compounds with fewer carbon atomsOHON+OOd) (cinnamaldehyde) from organic compounds with fewer carbon atomsOH8. BONUS: Aromatic rings with electron-withdrawing substituents can actually react withnucleophiles, by a process called (not surprisingly) nucleophilic aromatic substitution. Thesereactions are discussed in McMurry but we did not discuss them in class to avoid confusion withelectrophilic aromatic substitution. An example of the nucleophilic substitutions is given below. N+O OClN+O OOHboiling, conc. NaOH,then neutralizea) Propose a mechanism for this reaction using your experience with other mechanisms and theidentity of the product to help you. (8 points)b) Under these conditions, m-nitrochlorobenzene does not react (it must heated to about 300 Cunder about 100 atmospheres of pressure to react). Use the mechanism you have proposed toexplain this difference in reactivity. (8