sample_test Midterm 2 key

sample_test Midterm 2 key - Chem 118C / SSI / 06 / Sample...

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Unformatted text preview: Chem 118C / SSI / 06 / Sample Test-II / Nambiar \ ' fanned in the following . , . Dr w the stmcmre of the expected orgamc product (5) . ‘- ézgtgofif.)Unl:ss mentioned otherwise, you can assume that all reagents are present m - - « excess. If no reaction occurs, wnte "No Reacuon . 1. 2 equ. Em [A I 1‘ ©O 2. 'NaOH - a I R~€Hg€ngW£L 1. NaCN; 2. LiAlH4 R-“CH Br 2) 2 3. H+ / H20; 4. K2 CO3 / H20 1' CH3‘ (3 {ls-CH $059+ “323 2. AggO/HZOIA 3) CH3-CH2-CH2-NH-CH3 ' H OH ' P -r CH3 605‘” © (CH300)20 (1 oq) / H20 IA . 0 4) 6H3 ~60 “m 61+?! = - . ' H“ I :Q - OH abéfiiozECH-CHz-Br f ' 3—81.! 5> 6; —————+ a - 3.A LNaOH/Brz fl__ MH£p_€ H3 6) R—CO—NH2 .2. CH3COC1 7) ©NH2 1. NaNOz/HCl/OOC 1397/34 2. CuBr III. (20 pts). Show how you would carry out the following transformauons snowrng me reagents you would use in each step and the structure of the intermediate products {om 1. OH OH \K‘flg 0‘2 0 / o if? g with W) 0 . 2 R-CHzCl R-CHz—CHz-NH—CO-CH3 . I < I l/ he” 9pm,, c, “be” {’4 New 279:0 “flaw”? J 0 0 d5 b’CHzMCHah (399p @1753 N H ' W.“ . (14 pts).An unknown compound A (C12H1502N) gave the proton NMR spectrum shown below. Upon boiling compound A with aqueous sodium hydroxide solution (6M), and then acidifying with aqueous HCl, a white precipitate was formed which was filtered and dried to yield compound B(C3H302). To the filtrate, aqueous K2CO3 solution was added until pH = 10 and then extracted with chloroform. The organic layer was dried over anhydrous Na2804 and evaporated to dryness to yield compound C (C4H90N). Deduce thestructures of compounds A, B and C. v. (10 pts) Provide a systematic name or draw the suuctuxe as appropriate for the following compounds. ‘ 2. N-Methyl ethanamide C HJ-{f 0— N H «(P H 3 3- CsHs-CHz-CHz-N(CH3)2 N; IV ‘ 0L.W*él* Mwmdm . 4. m-Nitrophenyl ethanoatc 6’ H5 "60 fi 93\ 5. Br—@-—NH2 A —— ' Vla) (5 pts) Rank the following compounds in decreasing order of basicity. NHZ NHz NHCOCH3 . NH: é - b] CH3NHz © , N02 N02 ' A is c D E ' J) A E 8 . > C. High Basicity Scale Low b) (5 pts) Rank the following compounds in decreasing order of Acidity OH OH . OH OH ' ©‘Q Q; ©\CW . ' N02 N02 3 A B C D E _B})29>C>E ...
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sample_test Midterm 2 key - Chem 118C / SSI / 06 / Sample...

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