Midterm2 Fall09 key

Midterm2 Fall09 key - CHE 118 C- Fall 2009 Instructor:...

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Unformatted text preview: CHE 118 C- Fall 2009 Instructor: Nambiar Second Midterm November 20, 2009 This exam contains six pages and six problems. Please make sure that your copy contains all the six pages. If there is a problem, please let us know before you start answering. Please answer all questions. TA: Lab Section: _ — _ page 1 I. (40 pts). 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 ‘ ll Reaction . “P 0 0 N ~ 11+ 1' H H H3C/U\O/U\CH3 \W «1- C/Jfife 1 equivalent Liv 1. CH3| ~+ 7) 2. A920, H20, heat 1. NaNOZ, HCI, o c /- G it'd/VH1 2. NaCN 13/ 3. H2, Ptoz, CHSCHZOH 1. RANHZ H+cat. g _____-.__———> 2. NaBHaCN 3. H20 0 Ncho3 2N\ E /\O NH2 m» NH2 3. 0 do: : O OH OH H 5. HO 1. NazCr207, H2304, H20 6. 2 heat / o 1. NaOCH 7_ H COMOCHa 3 3 2. NaOH. H20 0 3. 1130+, heat C) 8_ A 1. n-BuLi /1CL , SYS 2 CI R ' Q (:9 3. H90, HgCIz/fia V I O 9' MQ/ VK " 50—3 3 NaOCH3 HOCHa, heat 0 10' ANHZ + 0/4 2. CHaMgBr II. (20 pts) Show detailed reaction mechanism for the following, showing the structure of the expected products. 69 IR 1‘ N . . 2 H C» thiamine - ; KOH ’i’ (L , #043 > flf 6’” + ,& “.6, lat/(57% 2% ll 9 (a «/ ~43 ‘ W” 4 M010 67” \R‘ 4 ll: 5L 0%” t 5313” 9“ A "’ 0‘ «t ‘ (Far 15:0 6 Chi/If. H ,0” d 1’: [U P: 63‘ ml 2 HM H*c:talyst E? 11‘ y Heat: EM #fl/ I 1 H 'L :3? Wm g/Ug ‘ )1??? fit III. (10) Show how you would carryout the following transformations, starting from the following compounds. You may use any additional reagents necessary. If the process involves more than one step, show the reagents used and the structure of the product formed after each step. Only steps productive toward synthesis of the final product would receive partial credits. O N 3,0” o page 4 MM N— I H 2. N-ethyl-N-isopropylbenzy|amine F ’\ fl , i 7 i . ~ ’1‘ - 6 #6» o N NH * r 3. 2 O 2 f fimMn/LO C’lnM COOH “~69 J 4. Ethyl 3-oxo-4-methylpentanoate "L, Carl 3) 73 5. Methyl m—bromobenzoate 627/ V. (8 pts). Rank the following compounds in decreasing order of acidity. O o J O 0 OS 0 O O O M F OH \/U\o/ /U\OH I \/U\N/ Mel H’U\/ I A B C D E F G H 0‘ LD>A>62>H>C> F>g ? ‘ Most acidic Acidity Scale Least acidic page 5 VI. (12 pts) Deduce a reasonable structure using information given below. IR Spectrum: Strong absorption bands at 3100 cm’l, 2950 cm'l, _ 1735 cm‘1 ,and 1650 cm‘1 Chemical Formula: C] 1H1 1BrO3 ‘2 3 / a @J /»*:x /9‘§ \ 1 , I» ,_/ 11 1 } 9 8 7 6 S 4 3 2 1 PPM page 6 ...
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Midterm2 Fall09 key - CHE 118 C- Fall 2009 Instructor:...

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