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322bs05_final_key

322bs05_final_key - 4 Organic Chemistry 322 bL Spring 2005...

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Unformatted text preview: 4 Organic Chemistry 322 bL Spring 2005 Final Exam May 4, 2005 Name Initial of Last Name 1. (40 pts) 2. (10 pts) 3 (4 pts) 4. (10 pts) 5.____________________.__ (14 pts) 6. ..______ (12 pts) 7.________________._. (10 pts) 8.________________________ (25 pts) 9._____________________ (10 pts) 10.____________________ (20 pts) 11._________________ (20 pts) 12. __ .______ (10 pts) 13. (10 pts) 14._______________________(10 pts) lack 1. Write the products of the following reactions. Answer 20 out of the 21 Questions. If you answer them agonly the first 20 will be graded. (40 pts.) Cr 1”“ a; CHZ-C-H NH3 CW; "H- HOO HON ' Ho an O Q 0 (E3 (5 [(CH3)2CleN‘9Li9 A 53 (veer [é a O 1) Ph—SeBr .. g + 2) H202/room temp é +W 0 0 3/053: iii A + EtO-(IIJ—OEt——> é ‘ci—M m. Q LiAIH [O-C(CH3)3]3 No2 07’ h. —QCH—CH2f\r— iii.» .‘(Cfl—lCHA’n n HCI emu p. CH2=CEH H202/Fe+2 / Cl o o Co \ u u \ 1E5 ( W q. PhCHZC-OEt + EtO-GOEt pkg,“ toga W (914) N +'+ a ‘u’ t + gowm 3 Use the circle method to draw the relative energy levels for the cyclopropenium cation. Label these bonding(B), non-bonding (NB), or anti—bonding (AB) as appropriate. Comment on the aromaticity or lack thereofthe cyclopropenium cation. ( :pts.) l0 Draw the isoprene units in geraniol, which is found in the fragrance of roses. (4 pts.) 4. Comment on the factors affecting the length of these two carbon-nitrogen single bonds. Consider both hybridization and resonance. If resonance is important, be certain to draw structure(s). (10 pts.) COQH Cholic Acid H0““ Draw the chair conformation of the A, B and C rings of Cholic acid. Be certain to label the substituents (methyl and OH groups) axial or equatrial as appropriate. Specify to which ring this arrangement (e or a) is made (14 pts.) ta Give an example in the form of a chemical reaction which utilizes the following reagents. Be certain to indicate stereochemistry if appropriate. If it is a protecting group be certain to “w mater at 2i?” “1 B a. Deacylase H vu/ g0» €03: ‘ p z _ 6’) ,_ ,. " \ 04A50~ NP‘H H4143“ A CE VH5”? W H (7 9) wt, 0 0% 0% Q offioflyfité“ / / \ U67 ‘ / \i b' CHao OCHs fig @159 was: \‘ \Rfi' ’1 (“c/x © (III 6 VB” L’Aopi Ho 0 C O l by“ ' cam—cit! 0 “‘3 COM || ‘3 O OCHz—O—C—CI 9 Ci @ mic/E’MW'C’W d. W N,,C,W _____.J g ‘ i 5 tilt/3M Vitamin A Prepare retinal from vitamin A. Draw chemical equations to show how retinal interacts with the protein opsin to form rhodopsin. (1 0 pts.) L" 8 3’ 3M ww‘mxs 0’ ¢9C~’1Le/ The following re ents are used in peptide and amino acid analysis. Uselchemical 16‘ reactions to how you would use each. What information (viii you 0 ain? ($696.) RQSWW" SDMX 0Q ép . icng AD 9\\ 57k W ‘7 Q‘fls 9‘12, be. ‘wg, aQ-hQWmAIm 'M . 3 I ' @‘Nfl Nka/M‘m emmD act "a K I l r ' w" a o (2% 'C a”)? V c. Carboxypeptidase v 629$ C'- wm'iwp amino 95:3. saaww 11‘ ’ w atoaofiUez. 10. CI 3 © figmu sfwiw Write the product(s) of this reactiion. What is the name of ti; reactive intermediate involved in this reaction? (10 pts) 8: [92’3é27m2d '1» Z‘»7L~k('l4~\ «£0 Given benzene, 1—butene, and any inorganic reagents you need, prepare n-butyi benzene. (20 pts.) m When the terpene citral is allowed to react with olivetol in the presence of dilute acid , a /‘ mixture isformed. Among the products is racemic A1—3,4-transtetrahydrocannabinol, one of the physiologically active ingredients of hashish (marijuana). Write a mechanism for th's at'on. (20 ts. I re CI p OH m t ' 9 W ~.‘ _|‘i_> H HO CsH11 . CW olivetol O C5H11 Hint: A key intermediate in this synthesis is Be certain to show how it is formed from citral. OH 12. Write the products of five of the following six reactions. If you do all six only the 1stfive will be graded. (10 pts.) a. PhZC=O + CHa-CH=PPh3——> PMCA 6. ’0 £0) Mf— Me fl 1) H B 3““ «OH / . ‘l b. 3 \ a“ l fig: dc) O O 9 \\ _ _” OEt ; "C\ c cw H+ @ rm. @w an i 12 13. Draw the molecular orbitals of 1,3-butadiene. Place them in order of increasing energy. Label these bonding (B), anti-bonding (AB), or non-bonding (NB) as appropriate. In a disrotatory process determine whether W2 is symmetric or anti-symmetric. (10 pts.) B . ill/kfiYEL 7“ 14. Work out the sequence of amino acid residues in the following decapeptide whose amino acid composition is Arg, Cys, Glu, Glyz, Leu, PhezTyr, Val. Partial hydrolysis of the decapeptide gives the following five tripeptides whose sequences have been determined ValesGly) GlyPhePheJ GIuArgGlyJ Tyr Leu Val ) GlyGlu Arg. (10 pts.) ...
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