Epoxides PS Soln

Epoxides PS Soln - Epoxides Problem Set 1. Epoxides that...

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Unformatted text preview: Epoxides Problem Set 1. Epoxides that can exhibit chirality are always a cis-isomer, like cyclohexene oxide, shown below. Why”.’ O '“u 5mm“ amide would Lx lav Slammed h: ems-l- / '0‘ "33;" Banal Cacn't {‘2an around “L'wa 2. When an epoxide is opened by a negatively charged species (A'), the reaction always goes through something called "backside attack,“ which leads to the trans product, as shown in the reaction scheme below. Using this information, complete the following reactions, giving the correct stereoisomer for each one. 1. NaOH q 33$. 2' W ’5: I la a. "D D” e. a” Br 1. Nags Q NH5 2. H+ (excess) " Zn 5” 7; N h. f. o“ “1. 1 NaCN H NCH W —+2 3 5:. m ’ M an C. g_ ‘39 u } @ ;. EEOCHg Break Makc ’ 2 am 3% c—u 354, d a“ DC”; Hvkl 9% 0—H» Liar ‘l‘IS 3. For question 2(g), calculate the AH” for the reaction. 4. We talked about the reaction of ethylene oxide with sodium hydroxide to make ethylene glycol. Under different conditions, sodium hydroxide can start a polymerization reaction of ethylene oxide to produce polyethylene glycol (PEG, usually with a number following to indicate how big the polymer is; e.g, PEG-40 has 4-0 ethylene units in it. These are very common in consumer products of all sorts]. How can you adjust the reaction to create mostly ethylene glycol in one batch and polyethylene glycol in another? 0 i E condltlons? HONOH ethyleneglycol mac lm6\ (%M\\/‘bw '53 No.01" (or 211155). Tl“ £90706“: vs no.” r (9 0 conditions.) 0 {Pa‘ld;“ IrLl'D 0H. Y‘lbl‘ OWK { 5 ' HO OH PEG - n M‘f/wdimc Minimum a? 9016.711“ 44* A09 mu 4%! Z; lug.“ 2’; CM 79"; 9 ’\ OH \4') a“ a-bomd— r‘daJ-uw. Canard—raking! ...
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This note was uploaded on 10/24/2011 for the course CHEM 312 taught by Professor Bailey during the Spring '03 term at Cal Poly.

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Epoxides PS Soln - Epoxides Problem Set 1. Epoxides that...

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