final exam - NAME(please PRINT Chemistry 109B FINAL Exam...

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Unformatted text preview: NAME: (please PRINT) Chemistry 109B FINAL Exam June 10, 2010 0— Value Total Score 1. 10x8 80 7 4x5 20 -—3.— 4x8 32 T 4x4 ' 16 I —5-.—10+6+10+8l34 I :— 6+12 ‘ 18 ~ _7._ 1x10 ' 20 l '— l | 1. Provide the major organic product(s) from the following transformations (in the boxes provided). Be sure to include stereochemical information where appropriate. [10 points each] 0 O 1. LAH, THF (a) —————————-> 2. cyclohexanone, cat. H+ (b) COOH 1. SOCI2,CH2C|2 —-———-———-——-——-——-—-—-—-> 2. n-Bu2CuLi,THF,0*C 1. Mg°, Et20 (c) c: —-—-——--———> 2. (>02 3. H30“ 1. HSMSH ' cat. BF3'Et20 (d) O —-———-—_* .,’ 2K 2. Raney Ni '1 3. BT2, h‘V Et2NH, CHZCIZ e ——-—-—-———> ( ) n § 1. BH3, THF —) (f) 2. HO", HOOH 3. H2NNHPh, cat. H+ IDIIIU 1. H2,Pd/BaSO4,quinoline 2. NBS, CCI , (g) —'-———iA————-> 3. Mg metal, Et20 4 DZO O 1. NaOMe, MeOH h ——-—————> ( ) 0 2. PBr3,CHC|3 O 1. NaH, C32 ‘.“‘ 2. Mel .‘ ________.—+ 3. A OH NH2 300121. 1: E 0!; 2. DIBAL -78°C, CH2C12 3. 1130+ 2. Provide the reagents needed to convert each starting material or intermediate to the products shown. NEW 0 Ph OH E E i 3. In each reaction there MAY be an error in the chemistry. Given the starting material and reagents as shown, suggest the nature of the error. If all as written is correct, write "correct." 0 1. LDA, THF/t-BuOH, -78 °C ————————) 2. Mel CH0 1.NaBH4,EtOH o 0 a» W _—————> WV f '- ‘- 2.Ac20,pyr ‘ '- 1. H30+ 03 ————-———-—-> OH HO“ O 2. HON cat. 1. DIBAL toluene, 0°C 2. Zn(Hg) HCI OMe 4. Azithromycin, the antibiotic in a "Z—pack," has the structure below. Give the oxidation state at each center labeled 'a' through 'd.‘ sugar-O Q—sugar O D. 5. When LAH reduces ester A the resulting product B can then undergo a \Villiamson ether synthesis to methyl ether C. On the other hand, when amide D is treated with this reducing agent, a different type of product E is formed. Exposure of E to H3O+ leads to final cyclic product F after workup with mild base. 0 N03: LAH O O V Williamson ether synthesis _ A LAH —> H30+ then workup with NaH003 NH2 0 a: (a) Give the structures for products 3 and C. (b) Provide the reagents for converting B to C. (0) Suggest a mechanism for generation of product C from B. (d) Provide structures for products E and F. 6. There are several omega-3 polyunsaturated fatty acids (PUFAs), including DHA, EPA and ALA. One source of omega-3s is fish oil. PUFAs typically occur as their "triglycerides" (esters of glycerin shown below). Both the acids and these high molecular weight triesters are nonvolatile. Using simple organic chemistry, how would you treat such a triglceride (e. g., G, of DHA) so as to be able to distill, and thereby purify, fish oil? In other words, how would you react G to derive a far more volatile, distillable, fish oil? Provide a mechanism for this conversion. OH Em OH glycerin ' 7. [Extra credit question] In one textbook students are asked two questions relating to carbonyl chemistry: (1) Which compound would you expect to have a higher dipole moment, methyl acetate or 2- butanone?, and (2) Which of these two would be expected to have the higher boiling point? 0 0 AO/ */ The answers given in the corresponding Solutions Manual indicate that for (1), CH3C02CH3 is the more polar due to resonance, and for (2), the intermolecular forces holding CH3C02CH3 together give it the higher boiling point. Explain why, in fact, the correct answers are just the opposite: the ketone is the more polar of the two (dipole moment 2.78, vs. 1.78), and the ketone boils at a much higher temperature (80 °C) than the ester (57 °C). ...
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