2005_pracmd3_key - Chem 118C / SSI / 2005 / Sample Test-III...

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Unformatted text preview: Chem 118C / SSI / 2005 / Sample Test-III / Nambiar L x . Draw the structure of the expectefi organic product(s) formed in the following reactions. Unless xyentioned otherwxse, you can assume that all reagents are present in excess. If no reacnon occurs, write "No Reaction". Cr03 / H” / H20 1) , ©011on ____, 65.0 H 3 I. CH3MgBr ($915 2) CH3-COOR _____, (“Hf—C ——DH 2. H+IH20 (£93 .4) . 0 . 1. NaOH all . 5) ©_ 0H 2. c0; a 00% -——————+- 3. CH3OH/H+ 6) LNaNOleCl/00C 6/ 2. CuCl. 60°C H a H “‘"—"’ "0",. 0% I' 1. —B IL‘thi I. I? 8)‘ A . m_ a_ Peg/3 9/ 3‘“. HgO/Hgdz/H'T'o NaOH/Biz/Hzo {) 9) RCONHz '\ Na. 10) (CHsCO)20 (1 equivalent) II. Show detailed reaction mechanisms for the following reactions, showing the structure of the products formed. H+ ‘ 1. HO-(CH2)4-COOH , “0/4 , - 3 bun ’H‘ O H of)?” DH \'~' + ‘ 57 4 " Jr ‘5” 1:7 «r H 2 20H HIO4 / H20 / A ‘ ‘ . V ' fl (DH-ab H m/Ha‘? C H3 K '3' 0’0“ \ wolf—0w 0“ 5 g h 2K 68“, ’ a 63:0 893 + ~9\ 323:: 0 -—:7 3 -~ g ‘70 —>; ELTO- 15‘ \ofll wrap-0 HWH p15 :5 ‘ (hm ' E H \0 H 3’. R-COOCH3 + CH3NHZ ___, 9:7“? (jg-066i A _? " afi‘gege’ V” p‘ _1\ . J g _ wows T— W“ a- L set-3W1 "r '4; 0’15 i?) III. ' Circle the compounds that'give a positive test for reducing sugars. <32ng HO O 20H OCH3 OH CH3CHO CH3-CO-NH2 C6H5COOC5H5 N Q OH IV I Show how you would can-y out the following transformations showing the reagents you would use in each step and the structure of the intermediate products formed. V. (30 pts) Provide a systematic name or draw the structure as appropriate for the following compounds. 1. (Mm-X 2. Dv-Cflg Ax" -.~ Mtg/9% (A3Lt/W9fc‘9’w9i 3. CI-Ia-CHz-CI-I(Br)—CONHCI'I3 {V ~ #0155: 58-254mmch ~4chzggmmmu2&3 Hon .. r. r l/7 _ 1 _ 4' HH m3 '— Lb //z-¢:«-/th¢:rzea§ 29(1 i OH I s. Benzoic Ethanoic anhydride 6. N—Acetyl-p-nitrobenzenamine Wfig ’WZQ” V, Rank the following compounds in the decreasing order of acidity. OH OH OH OH I @ CH30H aracoon ' N02 CF3COOH N02 0 a: 3 AB'C D B.FG — . NH: NH; N32 CH3NH2 VNH3 CH3CONH2 K . L M ’ N02 3 ' ' CH3CONHC0CH3 H ' I I ' N 5' > [:7 I“? >352 14) <7) E“) >1, H 7 .1) / A, y /< 5’ _ VI. - . .~;_.1‘he proton NMR spectrum of an unknown compound A (C7H1302N) is shown below. Compound A on heating with aqueous HCl (6M) gave compound B (C3H502) and compound C (C4H90N). Compound B up on reacting with methanol in presence of a strong acid gave compound D (C4H802). Compound D on reacting with sodium methoxide in methanol gave compound E (C7H1203). Compound E on heating with dilute HCl gave compound F (C5H100) whose proton NMR spectrum is given below. Deduce the structures of compounds A through F. J?" m. summed § 3 a E 5 ...
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This note was uploaded on 01/16/2011 for the course CHE 118C OCHEM taught by Professor Nambiar during the Summer '10 term at UC Davis.

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2005_pracmd3_key - Chem 118C / SSI / 2005 / Sample Test-III...

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