Test 3 Solutions - Introduction to Organic Chemistry - Summer 2008 | CHM 122, Exams of Organic Chemistry

Download Test 3 Solutions - Introduction to Organic Chemistry - Summer 2008 | CHM 122 and more Exams Organic Chemistry in PDF only on Docsity! Summer 1 Test 3 8/4/2008 1. (10 pts) What effect would you expect the following changes ta have on the rate of reaction on sodium iodide with 1-chlorobutanc in diethyl ether? Sh t Nee a. The concentration of the halide is doubled, cake doable ° Sy I? halide ». The concentration ofthe indide is halved, tate Walve d cate KATES] 2. (8 pts) How might you prepare the following molecule using a nucleophilic \ substitution reaction? ‘ dte a kesh € wee ae ; ots” ME MF fair 6 ame, wn leaving, Man ‘ wo Sp> , ane: + tondibions 3. (8 pts) Given the following sequence of reactions indicate if the products are optically active by using a check for optical activity and an x for inactivity. of oO ‘ v x x ° “i 4. (15 pts) Draw the saw-horse projection leading to E2 product. Put ihe number | carbon “in front” and number 2 carbon “in back”. Draw the expected product as well 05M KQrBw Fr, > 18°C 4 ' Gy ~ L Cl eye dun ct ~up 5. (15 pts) Given the following reaction draw the mechanism that leads to the observed products. Indicate if this Sn, Sn2, E1 or E2. > che 4 A.M NaQEt in 80% aqueous ethanol at 160°C, * en | Penh ' rer olyne east sub. ao “ By 4 al Kena sas east N nfl 12 Sup b A D@ jor at ry HG mest 4 “Treble. bat cation Ge +o Ey. ne E, patie Gormed Ba 50 goer E, 2 wa ¢  Set 2 Set 3 140 10 b ge & > fard fo. assign bet order is bare see: Reutive wtensty 8. (20 pts) Provide a structure for the following unknown yielding 4 molecular formula of CH 90. d siles 2700 orp inte FG Rro-k po <n (ta) | Chain (too symactey al lS from BC) myn * Parent not observed me wn wo ta oo? 20s 0 eo ss 23.0 elo Base 45 go as. 32.0 12.3 3.33 ayaa 2 Ve Bo 88 also see 54 uo . Gd 0 ra 5 tet 3 : 3 3 5