Q2Key_Wi05 - NU Winter 2005 Quiz 2 Chem 210-2 2 1(20 pts...

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Unformatted text preview: NU, Winter 2005, Quiz 2, Chem 210-2 2 1. (20 pts) For a and b, gives the IUPAC names of the structure shown. For c-f, complete each of the following reactions by providing the missing starting materials, reagent set(s), or product (only the carbon-containing major product is necessary). If a reaction does not occur, please state so. Your answers should be consistent with any stereochemistry that the reaction may require. 2 - 9W. _ {[email protected] Br 0—— Phnvv ’M—MQO’W‘W l ‘ N02 0Q. ‘. A,- Q/W ~ 3~ g/LMMXL mtOgWZ’l/v‘k M C. ‘ mflaflwyéi‘a‘W)W “WM @113“ B 1)1 equiv so3 in H2804 0") ll go; H :j isolate the most sterically hindered product 2. 2) HNO3, H2804 isolate the most sterically hindered product 3) Brz, FeBr3 O 4) excess KOH, heat d. 5) N32CF207, H2804 l) C21 )ch} OH 4% Q 2’) @H)A)C/ %) 05 C)Na(1i+4 04cm, OYL 5) Numb )Mwur e. Alfie’s—’1 é) [4‘50“ Woven w OH 3) W03 )Z‘EL 4-K“? Q 3,) 4303)) um W M a) UHL~M1L) buJA I NU, Winter 2005, Quiz 2, Chem 210-2 3 2. (10 pts) Propose a reasonable mechanism for the following reaction. MD M (3 $5M W ’5wa CEO> + Hjm HCI C'\/©::> + H20 NU, Winter 2005, Quiz 2, Chem 210-2 4 /f\ 3. (20 ts). From benzene as a must-use starting material and any other carbon-containing starting materials with 4 carbon or less, propose a synthesis of the acaracide (an agent that kills mites and ticks) and fungicide dinocap. You may also use the Swern reagent (dimethyl sulfoxide, NEt3, and oxalyl chloride), NBS, tosyl chloride, TsOH, pyridine, PCC, mCPBA, peroxide, and any inorganic reagents. ...
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