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Unformatted text preview: cumwaa dance. Meow rag (9.39 5. Identify the predominant type of mechanism for the following reactions (5N1. 3N2, E1. or E2). :1. l-bromobutane + NaN; -) l-azidobutane g” 2 f I. I”): b. bromocyclohexane + NaOH 9 cyclohexene E?" c. 2-bromo-2-methylbutane + NaCN "9 2,2-dimethylbuzanenitrile 3“ l " t 3' R-Y . . . (lam: 2-04 > 6. Predict the product(s) for the foilowmg reactions. ‘1“: a. I “\‘H a“; ‘9 NaOCHZCH3 I“ —* / "fig-Er CH3CH20H b. cut stot, heat H ——'> 6% — T “a 7. Write the rate expression for an 8342 reactiOn and an SNl reaction, given the following generic reaction: Nu? + R—X —) R-Nu + X‘ 3N2: Rate: l; [ta-)5] [Nu '- ”] (LFMWB SN]: Rate 2 L 8. Radical chlorination of pentane is a poor way to prepare l-chloropentane but radical chlorination of neopentane (2,2—dimethylpr0pane) is a good way to prepare neopentylchloride. How do you account for this difference? (L (W M ___r, {all}; L/L L l‘meDnTM—vshu. . l“) cg “thisrx-«mSuQn-Jhmwhh (u..l—oLt--f-«-:} § 'S-CLmei-m) he 4, I’l'aJ-Ta-Qnmm {LO-«A. PW- ?“ or t"; ._.-"—::=- “arc-CW5 L.“ ‘11 l. W: ‘0 rm 'WL “a a“; Rmmfimal‘fl-K.mhamamt°ufim chm, flux “'9ththnd n an. «L3 w .. ._ - (no “Win-«lush uh&> inf-m. mm . YA- (Lug—Cfl'z-GH L 9 (12 pts). (Solomons, p. 323) Marchth ol lowincr reactants with ' each case would lead to the product propene a proper reagents that m by placing a letter in the space provided. 5‘ propyl chloride 0" P-wrc') (a) H‘, heat b “d ' - a ,___ isopropyl chloride (2 w) (b) (CHQCONa. (CH3)COH A propyl alcohol (II-DH) (c) H, Ni A isopropyl alcohol (9.4“) (cl) CHJCHloNa, CHJCH.OH 10. Draw all the producls for the following reaction- a4} 3r an 5.;- u on; Br; +- Bl Br CCL‘ ’7 .5 91' 9' 13. Draw structures for the following molecules: a. (E}-3-fluoro—3—hexene F\ ,H c.=c. / \ b. (E)-4-elhyl-3~heptene CA1, all; anal-I, -.-. c.\ u ’ ads-maul; c. (Z)-l-bromo-Z-chloro-2-fluoro-1~iodoelhene 1 \ fC—t C: C.\ / or F 15. What starting material and what reagents would you use to synthesize the following compound in one step? ’93-... - "* one} A A. 5 WM Han-J... \ 1..) 14,0.2'!‘ U 0 - ? 7 . . ——_> (,1 \ / i were due: III-:1— RM Ilium: Chemistry 2373 - Second Hour Exam Name: 3. Write a mechanism for the following reaction: C'JH H3C CHCH3 H 1- ——————* A H3C 0“ ©me 9 1) CH ‘CH; '9“... grim—0H3 '1’; f. mama; 1.0 awn-bum“ ghffi" (/{h OH @‘xcfi/ 3 H H '53 ‘ I ‘ L H18. CH“, CH \\ '3» \R @4. (a) A Call“) cyclozghene yields the same alcohol whether treated by BH3/H202, OH‘ or H“ so WW. What is the structure of the reactant cycloalkene and product alcohol? ' H OH Alcohol Cycloalkene (b) An isomeric Cal-1,0 cycloalkene yields one alcohol when subjected to anyone}, on- and a different (isomeric) alcohol when treated with H20, 11+. What is the reactant cycloalkene and what are the product alcohols? (There exist more than one possible answer. You are to write only one.) 1. 8H3, THF 2. H101, OH' 04 Alcohol I 3 H H*, H20 ' CH '3 Cycloalkene I" OH Alcohol II W) A) [7 points). By making use of curved mechanistic arrows to indicate the movement of electrons, and by drawing the correct structures of all the intermediates with the aggrogriate charges and the correct number of lone‘ gait-s of electrons, write a detailed stegwise mechanism, leading to the product of the following reaction. on H-(il: (3 1 M 9”»; " P 0? 8H C mchfiw ski Pr (Do not forget to show the correct number of unshared electron pairs wherever appropriate in you- mechanism). B) (6 points). Starting with‘cornpound (D that is shown on the left and making use of any known oganic and inorganic reagent. provide‘s'a stenwise synthesig of compound (9 shown on the right. [go got write any mechanism, but show the struth of all organic products that are obtained after every step 0 e synthesis). CH, CH: 1 CH: I .. Q—CH —CI'{23‘-:2 L1 mafia-1,0 Nd “gr. a'ha‘»0“ 0H5 CV 6.“:GH1 ...
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