Chem+118C+SSI+2010+Sample+Test-2+Key

Chem+118C+SSI+2010+Sample+Test-2+Key - Chem 11’8C SS 2010...

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Unformatted text preview: ' \ Chem 11’8C / SS] 2010/ Sample Test-2 / Nambiar @ 1. Draw the structure of the expected organic product (5) formed in the following reactions. Unless mentioned otherwise, you can assume that all reagents are present in excess. If no reaction occurs, write "No Reaction'.‘ 1. B /h 1. CéHs-CHz-CHa _._:2___v___ gCHtS “:8” 6 H9\ 2. NaOH‘ 1. N CN; 2. LiA1H4 2) R-CHgBr a a , GHaéC? *b‘A/H; ‘ 3. H20 ~ . 1. CH I , ,. a i + IV - 3) CH3-CH2-CH2—NH-CH3 3 0H3 6H ’C “51 @523 _ 2. Ag20/H20/A é) (CH3CO)20 (1 eq) IH20 IA 8/91, 4) . a .65 NHZ _ N H 50 3 " 1 - €15 . 5 ,_ 5+ J -B o o f ‘ 5) RCHzNHz n mylhflnum a *6 Hat” NH A + A151 . 1. MIN; fl/ éH‘j R- CH2B1' . ' . a __e H9! H 9\' 6) ~ 2.LiA1H4 7) m _. 555555555 ~ {WW’ZKI \ C3203 CH OHIi-I‘ ' 3 H 3 H 6 flé J ema ———- fivww; (:5 5/5 II.‘ Show detailed reaction mechanisms for the following reactions, showing the structure of the expected major product. 1. NaOH © 2. CH2=CH~CH2Br 3. A 0 .—— “ egafg '{”9\ #7 g + ”a 0 n (\g'n 1. tthe follo III. .Show how _you would carry ou reagents you would use in each step and the structure 0 a) 1. R-CHzOH I \Ggfie—QDC/R l 009/33 “(WA-Ell Qfl/‘liimH ézfllafl JHK R ell— 8h 7 a) W 2, OH OH {é CH2CH=CH2 015 V éf’fiiazwvew j W‘QH A IV. Provide a systematic name or draw the structure as appropriate for the following compounds. 1. o_NH_CH3' A/n NW W’QQMWQW'W 2. N—Methylethanamide 6 l3 ‘3 “NH W3 3. CsHs-CHz-CHz-N(CH3)2 W) {V’- :D ) MM? LWM Wfi CH ~c€-0—/a 4. m-Nitrophcnyl ethanoate V. .Rank the following compounds in decreasing order of basicity. ' NHz NH2 NHCOCH3 OH OH @5 a); @2— ‘Wéb ‘ V . N02 I. . COOH A B. C D E F ,D A>'6 -C>E>F. __._. High Basicity Scale Low VI. An unknown compound A (C10H120N'Br) gave the proton NMR spectrum shown below. IR spectrum showedstrong bands at 1650 and 1700 cm"1. Upon heating with 6M aqueous HCl a mole of compound A gave one mole of compound B (C7H3NBr) and one mole of compound C (C3H502). Deduce the suucmres of compounds A. B & C. l \\ “flu , @- v1]. Circle the com pounds that give a positive test for reducing sugars. / H CH:OH_ ._/ HO \\ k on CHa—CO 'NH'Z \ \ i / C6H5COOC5H5 ...
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