Practice_Midterm_2

Practice_Midterm_2 - Chem 118C SSI 07 Sample Test-H Nambiar...

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Unformatted text preview: Chem 118C / SSI / 07 / Sample Test-H / Nambiar I. (30 pts). Draw the structure of the expected organic product (s) formed in the following I _ , reactions. Unless mentioned other-wise. you canassnume that all reagents are present in excess. If no reaction occurs. wnte "No Reacuon . ‘ i; 1-' "'2 eqiv. Brz , A 1' . (QC) 2. NaOI-I ' J! 1. NaCN; 2. LiAlH4 2) R-CHzBr ' 3. HUI-120; 4. K2 CO3 I H20 1. CHgl 3) CH3-CH2-CH2-NH—CH3 . 2. Agzo I H20 / A on (CHSCOho (1 cc0/1320 IA" 4) NHCH3- ' OH 1. NaQH ' v . 2. CH2=CH-CHz-B 5) _________, ' 3. A 1 . NaOH / Brz 6) R-CO-NHz .2 . CH3COC1 7) ©NH2 1. NaN02/HC1I00C 2. CuBr H. Show detailed reaction mechanism for the following reactions. 9K0” 4. a 2 H ‘ . ".7 5k EEK/“l a; «~6_H&Bn ' ' "H 0 J) Nag—NH; 1. ou would carry out the following transformauons snowxng tnc and mesmmomc immediatwm romcd- ' 1. OH ——————r OH O 2 Rake! I R-CHz-Cl-Iz-NH-CO-CH3 J O O é b#m2N(CH3)2 IV. . (l4 pts).An unknown compound A (C12H1502N) gave the proton NMR spectrum shown below. Upon boiling compound A with aqueous sodium hydroxide solution (6M). idifying 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 ev to dryness to yield compound C (C4H90N). Deduce thestructures of compounds A, B and C. V. (10 pts) Provide a systematic name or dmw the suucmrc as appropriate for the following compounds. . ' l. O—NH—CH3 2. N-Mcthyl ethanamide 3. c6H5-CH2-CH2-N(CH3)2 4. m-Nitrophenyl ethanoate 5. Br—Q—NHz Via) (5 pts) Rank the following compounds in decreasing order of basicity. NH; NH2 NHCOCH3 _ NH2 ()5 (C5 CW2 N02 N02 ' A B C D B High I Basicity Scale LOW b) (5 pts) Rank the following compounds in decreasing order of Acidity OH OH . OH OH ' o a , I N02 N02 3 ‘ Hi gh Acidity Scale 140‘" ...
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This note was uploaded on 07/22/2008 for the course CHEM 118C taught by Professor Xichen during the Spring '08 term at UC Davis.

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Practice_Midterm_2 - Chem 118C SSI 07 Sample Test-H Nambiar...

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