c237_ch4-6_packet_B - cum/i237 =ClnA--b MW (gin-8'4) 5....

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Unformatted text preview: cum/i237 =ClnA--b MW (gin-8'4) 5. Identify the predominant type of mechanism for the following reactions (8N1, 8N2. E1, or E2). a. l-bromobutane + NaN; 9 i-azidobutane b. bromocyclohexane + NaOH -) cyclohexene c. 2—bromo-2—methylbulane + NaCN 9 2.2-dimethylbutanenitrile 1‘ ' ; 6. Predict the productts) for the following reactions. 0"“- > 0‘5 a. ‘ NH H NaOCl—I2CH3 ——> #4 "05* CH3CH20H b. H2804. hcal —'> 7. Write the rate expression for an 3N2 reaction and an SNl reaction, given the following generic reaction: Nu:' + R—X -) R-Nu + X' 8N2: Rate = SN]: Rate = 8. Radical chlorination of pentane is a poor way to prepare [-chloropentane but radical chlorination of neopentane (2.2-dimethylpropane) is a good way to prepare neopentylchloride. How do you account for this difference? 9 (12 prs). (Solomons, p. 323) March the followino re ' - each case WOUM lead [0 the pm : actants wuh proper reagents that m clLICI propene by placing a letter in the space proviclecl.‘.q __ propyl chloride (3) Hz heat CM“ I LL a“; W... can. t or ' - “1' and «1'19? ' lsoproPYI Chlonde (b) (GHQCONR‘ (CPmCOH . propyl alcohol (C) H1 Ni __ [sopropyl alcohol (d) CHJCHloNa, CHJCHQH 10. Draw all the products for the following reaction. Br; ? BI '- Er CC]; 13. Draw structures for the following molecules: :1. ('E]-3—fluoro-3-hexene b. (E)-4-ethyl-3—heptene c. (Zl-l-bromo-2-ehloro—2-f1uoro-1~iodoethene 15. What starting material and what reagents would you use to synthesize the following compound in one step? Write a mechanism for the following reaction: $I—I H3C (THO-13 H + ‘—-'——.- A 4. (a) A Cfiflm cycloalkcne yields the same alcohol whether treated by BH3fl-1202, OH' or mm a _ WW. What 13 the structure ofthe reactant cycloalkene and product alcohol? - - Cycloalkene Alcohol (b) An isomeric C5HID cycloalkene yields one alcohol when subjected to BHy’HZOZ, OH‘ and a different (isomeric) alcohol when treated with H20, W. What is the reactant cycloalkene and what are the product alcohols? (There exist more than one possible answer. You are to write only one.) -—-———-—~h-— 2. H202, OH— H*, H20 -——‘—-—-—-——l— Cycloalkene Alcohol I E Alcohol ll IV) 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 aggropriaie charges and the correct number of lone Qairs of electrons, write a detailed stegwise mechanism, leading to the product of the following reaction. 9H HCl 1 (Do not forget to show the correct number of unshared electron pairs wherever appropriate in your mechanism). B) (6 points). Starting with'compound {D that is shown on the left and making use of any known organic and inorganic reagent, provide'n stcnwise synthesis of compound (E) shown on the right. {go got write any mechanism, but show the structures of all organic products that are obtained after every step 0 e synthesis). TH“ .. s“: One-m CH1 1 I! ...
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c237_ch4-6_packet_B - cum/i237 =ClnA--b MW (gin-8'4) 5....

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