documentview

documentview - SSN Name KEY FINAL HOUR TEST 1. (7) A...

Info iconThis preview shows pages 1–6. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: SSN Name KEY FINAL HOUR TEST 1. (7) A Haworth projection for the pyranose structure of a sugar that played an important role in Fischer’s determination of the stereochemical structure of glucose is given below. a. (4) In the space provided to the left of the Haworth projection, draw the structure of the sugar as a Fischer projection in the standard arrangement with the most oxidized carbon at the top and the CHQOH at the bottom. b. (3) In the space provided to the right of the Haworth projection, draw the sugar as the chair structure of it’s [3— anomer O\\ H C’ HO-CHZ OH HO H H H O H H (13H OH HO H OH OH HO 2 {o H OH ' H H H H CHZOH H H Fischer Haworth Chair structure projection projection “gamma 2. (18, 2 each) Below and on the next page is shown a collection of structures from classes of compounds which have been discussed during the second half of this semester. Some include additional important information in a caption. Each is designated with a large bold-face letter. Below is given a set of nine statements which may apply to one or more of the structures. Beside each of the statements given, write the letter corresponding to the structure that best fits that statement. An answer MAY be used more than once. Some will not be used at all. If there is more than one correct answer, you only need to give one. HO OH NH2 0 H H _"__ as oo 5”; B l I -... o 0 H2 N HH ll N\ CHZ‘O‘F'O'F'O' Glucose—1,6—diphosphate 3H H OH I HO HO formed during glycogen HO l HZN‘C / catabolism in muscles 0—3—01'1 0 NAD+ - Carries energy from HO 01—1 the TCA cycle by placing electrons in the pyridine ring. CAUTION: Non-standard drawing 0 /0' Na+ it C (i 9 O_$H2 One of the products from heating 0 — CHO_CH tallow with aqueous sodium hydroxide ,O*|CH2 Can be isolated from mostD l6 9 (9%] fast food hamburgers I") CHZ-O“P-O-—CH2-CH2-Il\l-H _ | - WC‘O_CH 6 E H WC/O—CH2 a cephalin Final Hour Test (b), Chemistry 302, Fall 2002. Page 1 of 6 pages ,CH3 H H~N N I HZN WN / 1 C1 0 j \ N [—12N/\/\1T1 F H )3 H Epibatidine-an arrow G O I ' H poison and natural pain Scopolamine-isolated from ‘C’C\H SPEFmIHS-found in most cells reliever isolated from the plants related to J imson 5 CH20H 0f mammals; Pellewfid '50 Play skin of an Ecuadoran frog weed; used to prevent a role Ill-CB” diffrentlation motion sickness and as 3. HO and PTOhfeI’aUOH "truth serum" in spy novels HO I CH2 0 H0 1-] H ' H CH2 H O O HO H OH H H H HO H L OH OH lactose-an important component of milk; some people, especially after F ucose—a component of glycoproteins Xylose-found in xylan from woods adulthood, have difficulty digesting it H such as maple and cherry; isolated H from corn cobs for use in tanning O O HO O and dying CH3 n ll (FH3 H - ‘ — /C\ ’C‘o~c—CH HO H O 0 CH3 CI 0 0 I 3 I H OH H H \CH2 cngo—c’ CH3 N CH3 HO 0 used to protect the amine M H H 0 in amino acids during Gaultherin-a form ofHO OH peptlde Synthems oil of Wintergreen that H H H H 0 O can be isolated from CHZVCH TL} Ilkg E the Wintergreen plant. 0 (l: U H\N F 11le ‘0 n S n 0 0 ¢l\ i R NomexTM, a heat resistant material E_E O N Material commonly that can replace asbestos in many Cl/ \Cl 131 Q used in gel 613cm)- applications such as flame-resistant d P It t. S-fluorouracil-a potent, phoresis for separating Clothing- use .as an a em we synthetic inhibitor of proteins to thlonyl chloride for . . . 0 makin ac l chlorides DNA biosynthesm that 18 H g y used to treat cancer C‘CH2CH2CH2CH2CH2‘NH n V 0 9H3 d t t “he am. A weather and temperature resistant _ _ use 0 P” 6° me la r th t 1 h l b'l't C1—C—O (I: CCIS T in amino acids during F0 5;;ge: a so as aw permea 1 1y CH3 peptide synthesis CH3 l CH2_C i? X (5“ C 0 0 Material used 0/ “O _ _ “ " for "timed" $132 C/0 CHZCHZO ll I I release of n W CH3 CH3 n drugs €32 n Z O _ ‘ OH PEN, a material that can be used for A “Ninja”? OCCUI'mg "PIaSth" that strong, heat and chemical resistant can be ISOlatEd from baCter'a SUCh containers that need to be sterilized as Alcaligenes eutrophus. using steam, Final l-lour Test (b), Chemistry 302‘ Fall 2002, Page 2 of 6 pages Z a. This structure is that of an AABB type polyester. N b. This compound is an anhydride of carbonic acid. D c. This compound is a molecule of fat. V d. This compound is an AB type nylon. G e. This compound is an alkaloid. K f. This compound is a D-aldopentose. L g. This compound is a reducing disaccharide. A h. This compound contains an anhydride of phosphoric acid. L i. This disaccharide is joined by a B 1-4 0 glycoside linkage. 3.(18, 3 each) In the spaces provided below, write stereochemically correct structures for compounds A - F. An optically active aldopentose, A, CSHIOOS, gave an optically inactive product, B, C5H1205, when it was treated with aqueous sodium borohydride. Reaction of A with hydroxylamine, NHZOH, at pH 5 converted it to C, CSHHNOS. When compound C was allowed to react with acetic anhydride in the presence of sodium acetate and the resulting product was then treated with sodium methoxide, it was converted to D, C4H804. Warming D with dilute nitric acid converted it to E,C4H606, an optically inactive c0mpound. Compound D could be synthesized starting with L-glyceraldehyde for which the structure is given below. Reaction of L-glyceraldehyde with hydrogen cyanide in the presence of cyanide ion gave F, C4H7N03, and an isomer of F. Treating an aqueous solution of F with hydrogen in the presence of a palladium on barium sulfate catalyst converted it to D. Similar treatment of the isomer of F converted it to an isomer of D. It is NOT NECESSARY to Show the structures of the isomers of D and F, that are mentioned. A SUMMARY [8 GIVEN BELOW. H\C,/0 H\C,/N—OH (kc/OH AW HO H C_ H0 H E* H0 H H0 H H0 H H0 H HO H HO H ,Cc / 0H CHZOH CHQOH 0 CHQOH “\Coo CzN HO H HO H H0 H B = HO H D = F : H0 H H0 H Ho H CHZOH CHon CHZOH Summary < 9; l? A NHEOH C 1) CHBC O CH3C~()-Na+ D HNO3/H20 E . + " C5H1005 pH 5 C5H11N05 2) CH3O Na [CH3OH C4H804 wan“ C4H606 NaBH4 H2/ Fri/821304 “20 HZO/H+ O\ H \C/ B _ + c H 0 HO H H'C=N/ K (Mm) F lsomer Hz/Pd/BaSO4 Isomer 512 5 + of}: -——-r—-—>HO/H ofD CHZOH (21mm3 2 L-glyceraldehyde Final Huur Test (b), Chemistry 302. Fall 2002. Page 3 of 6 pages 4. (1 l, the point value of each box is shown in the box) The Claisen condensation was among the most important synthetic reactions that was discussed in the fourth unit of the course. Its mechanism is exemplified by the following reaction. In each box, write the structure of the intermediate that would be present at that point in the mechanism. Be sure to show alt formal charges. 0 - u 1) CH3O Na+ ICI) i? CH3-CH2-C-O-CH3 ———T—> CH3-CH2-C-CH-C-O-CH3 O + :O= :E): H v H || | CH3-CH2-C-O-CH3 —- CH3-gH-C-o—CH3 <—->CH3-CH=C—0-CH3 be e :9'CH3 T II + CH3'CH2‘C'O‘CH3 . :6: 0 - CH 0 Q n <——~.3__ CH3-CH2-C—(lll-l-C—O-CH3 I go: CH3 (2) CH3 '- 0 II II CH3-CH2-C-CH-C-O-CH3 l Cngé-CH (2) “e :9: :9: :(l): :69: :9: + E) 9 CH3-CH2-C-g-C-O-CH34+CHyCH2-C—92C-O-CH3<+CH3-CH2*C=§j—C—O~CH3flbCHyCHZ-C-tZH-C-O-CHg CH3 CH3 CH3 CH3 (4) 5. (8, 4 each) Below are shown two synthetic transformations, each requiring several steps. On the next page are given five sequences of reagents, one of which would be expected to actually lead to each of the indicated products. In the space beside each transformation, write the letter corresponding to the sequence of reagents that would be expected to result in that transformation. NOTE: You are to choose your answer for both a and b from the same five sequences of reagents. one of the CH /CH3 sequences I 3 L 61- CH3CH=C ——> CH3CH2-C-CH2-NH2 \ of reagents on | CH3 the next page CH3 H\ ,CH3 with 335.22: t W B b. CH3CH2C ——-—--—>- CH3CH-CH \ of reagents on \ CH3 the next page CH3 Final Hour Test (b). Chemistry 302. Fall 2002, Page 4 of 6 pages A B C l) HCI / ether ])BH3- THF 1) HCl / ether 2) Na+ N:N:N' / DMSO 2) H202 lNa+ OH' 2) Mg / ether 3) LiAlH4 :9 3) NaZCr207 /sto4 / 1420/ 3) CO: + 4) H20 / H acetone (Jones' reagent) 4) H20 / H 5) Na+ OH' to pH 12 4) CH3-NH2 / H20 / pH 5 5) SOClz 6)CH3_Br/DN1F NaBH3CN 6) NH3 (aqueous) 7) LiAlH4 D 8) H20 /H+ 1) HCl lether E 9) Na+ OH' to pH 12 2) Mg / ether 1) BH3 -THF 3) C02 2) r1202 fNa+ OH' 4) H20 / H+ 3) K+ 'C'=“N / DMSO 5) soct2 4) LiAlH4 6) NH3 (aqueous) 5) H20 / H+ 7) Br2 /Na+ OH' / H20 6) Na+ OH" to pH 12 6. (6) The aldol reaction was another important synthetic reactions that was discussed in the fourth unit of the course. It can be used to make a five- or six-member ring if both of the carbonyl groups involved are at appropriate places in the same molecule. The mechanism of such a process is exemplified by the following reaction. In each box, write the structure of the intermediate that would be present at that point in the mechanism. Show all formal charges. 0 CH3‘E'CHZ'CH2'CH2‘E‘H flI-L—b H20/alcohol H OH "8 O l? :GH' 9 :9: (0: (I): ill: ll ll CH3‘C'CH2‘CH2'CH2'C'H r—"—> =CH2‘C'CH2'CH2'CHz'C-HHCHZZC—CH2‘CH2'CH2'C"H L :C:)H Final Hour Test (b). Chemistry 302, Fall 2002, Page 5 of 6 pages __E_ 7. (7) Below are shown the structures of seven compounds, each having molecular formula le-IIZO3 each indicated with a large bold-face letter. One of the structures gave the IR spectrum and 1H and '3C NMR spectra shown at the bottom of the page. In the space provided, write the letter corresponding to the structure of the compound that gave the spectra. You should recall that, in the IR spectrum, when an absorption is indicated by a tick mark along the bottom edge of the spectrum, the exact location of that signal is listed in the table on the spectrum. On the '3C NMR spectrum, the location of all signals is recorded in the table included on the spectrum. The lines marked with an asterisk (*) are from carbons bearing an odd number of H atoms. Tables of IR and NMR data are provided at the end of the test. 0 o I H0 CH3‘O‘QCH2—O—C: _O A 0 ocn3 06/ \ O CI-IZCH3 /, H'O D CH3—o—©—q F 0—CH3 ,9 O'CH2CH3 CH3CH2‘O‘©’CH7‘C\ E 0-H G in 21‘ 1‘ 1 LI 4 u i U Imclau. 1' I I 1! 11 I! ‘ll 1‘ 1| 1. W ‘I 1| II I! ll %ssmssmg z ' = i ‘ sass tsssss " mam-ma gi-i = seam-eases, " res—fissssss _ -- * assists srsamm: “ s.w ssssss " . iisiisiisiiiissiisusmas—1m . n w. .. isssnss I'lll'ttlll :. “smart! - l! maleiiiihsai I ‘ -;:' u m _ : I 7 i . p ; u i _ 5",“... ' E.17129. 1314.1 1102.8 MEL“ I ll . a; , m I I liflllfil. -u ‘ n "l" _ I*““151o.e 1153.3 fir-1.0 3 g : J I - I, -i;:—i-":”f;,9'b_j . . _ :----_.§_...._ ~- s...--- ~- a - a : 1“ w uum “aflfig'wi' NICOLET 293x ms ‘I’I .l 1‘. .| 5! n I . 19529 113.43- 153.13 can mar 5534' 122.57 mar CDCIB fi_____‘_________fi_ 4 to 1 0 Final Hour Test (b). Chemistry 302. Fall 2002. Page 6 of 6 pages ...
View Full Document

Page1 / 6

documentview - SSN Name KEY FINAL HOUR TEST 1. (7) A...

This preview shows document pages 1 - 6. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online