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Practice_Quiz_11_blank - Inside the shadow boxes indicate...

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Chemistry 322aL Practice Quiz 11 (1) Complete the chemical reactions below by providing the major organic product, as requested, within each box. You do not need to show byproducts of the reactions or any mechanisms. Provide stereochemical details in the products wherever they are important. (A) CH 3 CH 2 CHCH=CH 2 CH 3 (i) Hg(OAc) 2 /THF, H 2 O (ii) NaBH 4 , KOH (B) CH 3 CH 2 CHCH=CH 2 CH 3 (i) BH 3 .THF/THF (ii) H 2 O 2 , NaOH, H 2 O (C) OH + PBr 3 (D) C=C CH 3 H CH 2 CH 3 H + CO 3 H CO 2 - ) 2 Mg 2+ magnesium monoperoxyphthalate
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OH (i) NaH (ii) CH 3 CH 2 I A C 10 H 20 O CH 3 SO 2 Cl, amine base B C 9 H 18 SO 3 NaOCH 2 CH 3 C C 10 H 20 O H CH 3 CH 3 100% ee 100% ee 100% ee 100% ee (2) Provide the missing structures (A,B,C) inside the boxes below with attention to the stereochemical details.
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Unformatted text preview: Inside the shadow boxes indicate whether that particular reaction step proceeds by retention, inversion or racemization. (3) Provide syntheses for the following transformations. (A) bromocyclopentane trans-cyclopentanediol (B) methylcyclohexane (+/-) trans-2-methylcyclohexanol (+/-) (4) Reaction of 1-(chloromethyl)oxirane, labeled with 14 C as shown, with one equivalent of sodium ethoxide provides an epoxide with the isotopic label as indicated. Provide a reasonable mechanism that explains this result. ClCH 2-CH 14 CH 2 O NaOEt EtOH CH 2 CH-14 CH 2 OCH 2 CH 3 O...
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This note was uploaded on 07/22/2009 for the course CHEM 322AL taught by Professor Jung during the Summer '07 term at USC.

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