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l . Give the major product for lile following reactions. (3 points each) Ph 1. Na 'V"' oH ----- - 1. PhMgBr (excess) 1. Mg 3. W 1. HzCr04 2. CH3Mg81 3. H30• NaBH, CH1)H 2. l/lg Ph"' OH -------- 1. BrMg~ OH 1. TsCI, NEl3 N 2. NEIJ, heat 2. Give Names or stmctures for tbe following: (6 points) (racemic, not optically active) 3. For each of the following pairs , circle the one that is higher boiling and put a sguare around tbe one with tbe higher water solubilitv. (4 points total) b. ~OH ~O H 4. Rank tbe acidity of tbe following , from 1 (most) to 4 (least): (4 pis) o )l_ OH ~ ~O H 5. Circle which two of tbe following halides could be con verted into Grignard reagents that would not self-destmct? (4 pts) o ~B r 7. Suggest a strncture for an unknown A whose fommla is CJi ,0O and gives the following chemical test results. (4 points) Formula CJi ,0O Hydrogenation Test H,!Pt Chromic Acid Test H2Cr0 , Lucas Test HCl/ZnCl2 Reacts to give CJi 12O Stays clear orange , doesn't rum gree.n. No reaction. Reacts instantly, well within l minute 8. Provide th e mechanisms for the following reactons (4, 3, and 5 points) /'v' H-Br LJ ~ OH - Cfs, 1. Excess PhMgBr NaBH4 CHJC)H 3 !>. Provide the reagents necessary to accomplish tbe following transfonnations (4 points eacb) . You may use anytbing you wish, as bigas you like. (Note : the indicated number of steps does not include H,o• work"llp steps. Longer pathways may also be possible .) Note 2: If you can make something via ketone or vía ester, choose tbe ester . 4 Steps a b e d e f OH Ph~ o ~OCf½ ----------- - a, A Q-s r -------------- - CT'Ph~ ....____,B.,r. ... '("x:P h OH 2 2 2 3 3 3 10. (4 points) a. \Vhen an ethec solution of A, B, and C iin a separatory funnel is treated with neutral water , put a circle around each of thern that would remain in tbe ether layer .. (May be all, or more than one . . . ) b. When an ethe~ solution of A, B, and C in a separatory ñlllllel is tteated with basic water (NaOHl!!iO) , puta sguare around each of tb ern that would remain in tbe ether layer. HO~ v A o HO~ e 11. Design syntheses of the following. (5 points each). Allowed starting materia ls include any acyclic alcohol or alkene wth ~ carbons 5 1 l. Predict the 'H NMR spectrum. Include the approximate chemical shifts (l 's, 2 ' s, etc .), the integratiou , and !he splittiug (can use "s" for singlet; "d" for doublet; "t" for triplet' "q" for quartet; and " 111" for multiplet, anythiug more complex !han a quartet ; or you can iustead make a column to lis! the uumber of lines). Note: for siguals that are symmetry equivalen!, do uot list them twice . 2 . Predict !he "C NMR spectrnm. Include !he approxin1ate chemical shifts (220-160, 160-100, 100-50, or 50-0) and the splittiug if a couple carbou was takeu (q, t, d, s). 3 . Match !he following structures with the listed fearure IR siguals: 1) 1680 2) 1745 3) 3300-3400 4) 3300-2500, 1710 A B e D 2 Solve the strnctures for the following. If you gel a strncture perfect, you will get full credit . If you do not get a strncture peáec t, you may still get sorne partial credit . Thus, it is in your interest to show sorne of you work, make a stn1cture, or ·tell me what you kllow for mre. 4. C,H,00 3H, d, 1.10 3H, t, 1.30 2H, 111, 1.50 IH, s, 2.90 IH, 111, 3.90 IR 3300-3200 5. CJi 120 2 - - .......•.•..•. l .U IR : 1745 ) , 5 "e: 180 (s), 80 (t) , 35 (t), 28 (t) , 24(q), 19 (q) r ..J 1 ,.o 2,5 ......, 2, 0 .......1,._5 _, l . Of 1. ,0 3 - . ......... 1.0. .....P,I "' ' ·º' l . 00 4 6. CJi 120 2 IR 3300-3200, 1710 "e: 200 (s), 75 (t) , 45 (d), 40 (t), 30 (q), 19 (q) . C5ll·120z-.. .. . . .......... . . ..... .. . .. .. . ....... ... . . .. ... . • • • • • • • • • • • • • • • • • • • • • • • • • • • • • • ♦ • • • • • • • • • • • • • ♦ • • • • • • • • • • • • • . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ' . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ., . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ' . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ' . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .... .. .. ······· ... ·:·· ......... I ..... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . • • • . • . . • . 11--=-''-'-f.l . . . • • . . . . • . . . . . • - . • • . . • . . . . • . • . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .u. 4 ' ' 2 . IR : Notlling of imerest "e: 150 (s), 135 (d), 130 (d), 120 (s), 68 (d) , 40 (t), 25 (q), 20 (q) ·l,nH 16D···· · ····· ·· ···· • ··· · ··· · · · ·· · · · ···· ··· ·· ······ · ··· . . . . . . . . . . . . . . . . . . . . . . . . . . . . ' . . . . . . . . . . . . . . . . . . . . . . . . . . . . - . . . . . . . . . . . . -. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . • . . . . . . . . . . . . . . . . . . . . . . • . . . . . . . . . . . . . J . . . . . . . . . . . . . . . . . . . . . . . . . . . . . • . . . . . . . . . . . . . . . ·. . . . . . . . . . I . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . - '" . . . . . -. . . . . . . . . . . . . . . . - . - . . . . . . . . . . . · · · · · · · · · · · · · · · · · · · · · :11,1 · -· · · · · · · · · · 1 1· · · · ] ~ · · · · · · s 2' i 5 8. C,H,O (Two strucrures are equally acceptable for this problem) d d 7 9. C10H1,0 EreHl ll . . ... . .... . - • ♦ • • • • • • • • • • • • • • • • . . ' . . . . . . . . . . . . . . . . . . . . . . ' . . . . . . . . . . . . . . . . l . . . . . . . . . . .. . . . . . . J . . . . . . . . . . . . lft/ ;¡ 3 2 l. Provicle the Name for the Following (6 points) OH ~ o 3. Rank the followiing, with 1 being highest, or most. (3 points e.ach) a. c. o d. ~H o o EIO~ o o EtO~ Acidity Boiling Point Electrophilic Reactivity, \Vben Attacked by a Nucleopbile Relative amotu\t in tbe "enoJ• fonn at equilibrium 1 2 4. Synthesis: Draw the feature product of the following reactious (need not show any byproducts). NOTE: In every case, the product should be a stable, isolable product ; an «intenn ediate" stmcture or something that only ÍOllllS reversibly in an unfavorable equílibrium will uot receive füll credit. (2 points each) a. J__ e. f. lf' KCN.HCN HOCH2CH3 (cold, short time) (more synthesis, continued. 2 points each) g. h. l . J. l. l. l illA o o AAoE t l. NaOEt 2. BrCH, NaOEt HOCH,CH, (wannup, long time) l. PPb, /'-../'-9 , ----- 2. BuLi 3. C)=o 3 4 5. Provicle Re.agents for the Following Transfonna tions:: (4 points each) a. ;_O H--------. ~ o c. 6. For the following struc.nires, which will be "complete ly" (>98%) deprotonated by LOA (LiNiPn )? By NaOCfü? {Note: it is possible that more than one strucnire will be depronated.} a. By LOA? (3 points) b . By NaOCH,? (3 points) C)=o A 7. Designa synthesis for the following alkene, FROM ALCOHOLS WITH NO MORE THAN 5 CARBONS. (5 points) 5 8. Put in the starting materials for the following. (Note: May be only one chewical in severa! of these cases). (2 points each) a. b. c. d. e. o NaOCH,~ CH,OH u 1 beat NaOCH, 9. Suggest a possible structure for unknown X, whose formula is C6Ha0, given the following infom1atio1L (5 points) 1) It gives an orange precipitate upon treatment with 2,4-dinitrophenylliydrazine (2,4-DNP) 2) It does not give a silver mirror upon treatment with Tollen's reagent [Ag(NHin .OHl 3) It does react. \\~th excess Hi Pt to give C.sH1oO. 4) It does react. "~th excess Bn in dich!oromethane solvent to give CóHsBriO. 5) It does not give a positive iodofom1 test (NaOH, excess NaOH). Stunmary C.sHsO DNP-yes Tollens-no H~ -yes, to CóH100 Br2-yes Iodoform-no 6 10. Provide Mechanisms for the Following Transfomiati ons. (3 points each) (Note: in some of these mechanisms, either the reactant or the produc.t may not be a "final product" or an "isolable chemica l". But you should still be able to write the mechanisms.) O O NaOH O OH A. ll__M eOHA A O L IDA (LlNR:¡) O A 2. PbCH2Br ~ Ph O H• 60H HO~ l½O O ~ NaOMe Ph..,_/'-OCH 3 MeOH (Note: This process is central to íhe me.tabolism of carl>obydrates) 1. Name the Following or Draw the Strucrure (2x3 pis each) a. N-methyl-2-phenyl-l -butanamine 2. Draw the starting materials for the following hydrolysis reactious. (3 pts each) a. 2. HCJ b . 2. HCJ H Me ./'-..X ./'-..,O H HO _;;( ~ 7f H Ph O 3. Of the following, which fonn would actually exist at : ( 6 points) a) pH = 2 (acidic) b) pH = 7 (neutral) e) pH = 12 (basic) 1 4. Synthesis Reac.tions. Draw the feature product ofth e following reactions. (8x3 pts) o o Ph~ l. CIÁ._ 2. LiAll4 '-..,,,Br (excess) t laOH l. KCN 2. LWH, ./"-),.lO. _ l. NaOH ? SOCl1 V OEt - o 3. HO)l__ }½NMe J( NH _1._N_a_O~H u 2. H• 2 3 5. Provide Reagents for the Following Transfonnat ious (3x4 pts each) o-OH------~ '--./"- N ,..-..._.._ ~ o ----.)l_ NH2 ----- - 6. Compare the following nvo struc.tural isomers: (8 pts) a. Which of the nvo is more basic b. Which of the two is more stable c. What is the hybridization for the nitrogen Jone pair in A? d. What is the hybridizatiou for the nitrogen lone pair in B? 8 7. Rank the reactivity of the following toward sub stitution, with 1 being wost reactive. (3 points) 4 8. Provide Mechanisms for the Following Reactions. (16 points) )ol +P-.i.NH 2 NaOH Ph CI M"2N-H + 2 Me-1 + NaOH 8. Wbich (if any) after being dissolved in diethyl ether, will: (6 points) a) Extract into NaGH/H 2O? b) Extra et into HCI/H2O? e) Extract into neutral water? .,,,..._ CsH17 OH e 5 9. Rank the following in arder ofincreasing basicity, 1 being wost basic, 3 being least (3x2 pts) a. 'NaOH b. c. pyrid ine benza mide (PhCONH2) wethylamine 10. Rank the acidity of the following , 1 being most acidic, 3 being le.ast (3x2 pis) a. acetic acid 2,2-difluoroacet ic acid b. PhOH c. water p-uitrobenzoic acid benzo ic acid

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Organic Chemistry Questions Organic Chemistry Questions Organic Chemistry Questions
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