sampletest2key

sampletest2key - Chem 118C SSI 2008 Nambiar Sample Test-2...

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Unformatted text preview: Chem 118C / SSI / 2008 / Nambiar / Sample Test-2 I. (30 pts). Draw the Structure of the expected organic product (5) formed in :11: following motions. Unless mentioned otherwise, you can assume thzu all reagents 31: present in . ' ' excas. If no macan occurs, write "No Reaction". 1- 2 eqiv. Br: [A 1. (Ci) 2. NaOH 1. NaCN; 2. LiAlH4 2:. R-CHzBr __._.__________. R ~ (‘3 H976 HafNfiiL 3. H” IH20: 4. K2 CO: I F120 1. CH I ,. Ag 3) CH3-CH2-CH2-NH-CH3 3 C I 2. AgzO I H20 / A OH » PH _ 4) © (CH3th (1 equzoIA + CH3 605” M I J OH 1. NaOH v ' 5) . 2. amen-cars: H ’ . 3495c”; 3. A I . NaOH / Br; 6) R—CO—NH; [4—- A/ H "GO—Ca H3 . .2 . CH3COC1 7) @——NH2 1.NaN02lHC1IO°C 0 M _ 2. CuBr III. (20 pts). Show how you would carry out the following transformations snowmg me reagents you would use in each step and the structure of the intermediate products farmed 1. OH 2 R—Gdfiéfl/ R-CH-z—CHz-NH-CO-CI‘Is < 6% ‘6’ ix K 9L‘9flbq J 6” ' 3 o 0 W; . (14 pts).An unknown oompoundA (Cm-1150714) give the proton NMR spectrum shown below. Upon boiling corn und A with aqueous sodium hydroxide solution (6M). and then acidifyingwithaqueous Qawhiteprecipimtewasformedwhichwasfiltered and dried to yield componnd B(C3H302). To the filtrate. aquews K2003 solution was added untilpH= 10mmenemactedwithchlorofom1‘heorganiclayerwasdriedover anhydrous Nazimmmpormd to dryness to yield campound C (C4H90N). Deduee V. (1U pts) Provide a systematic name or dnw the 5mm 8 . following compounds. apprwnatc for the 1. O—NH-CH3 N— - 2. N—Mcthyl cthanamidc C HJ-{f 0-— N H—C" H3 3. C6Hs-CHz-CH2-N(CI{3)2 N, N ~41W—a— 4. m-Niu-ophcnyl ethanan 6 H5 ’60 "' @Da\ 5. Br._©-—NH2 A _. BMW . Via) (5 pts) Rank the following cpmpounds in decreasing ordcr of NH2 NH; NHCO CH3 . NH: 63‘ <33 Md N02 N02 ...
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This note was uploaded on 08/17/2008 for the course CHE 118c taught by Professor Nasiri during the Spring '08 term at UC Davis.

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sampletest2key - Chem 118C SSI 2008 Nambiar Sample Test-2...

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