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ps8 - mechanisms by which A forms B and C Your mechanism...

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Chemistry 3590 Honors Organic Chemistry I PROBLEM SET #8 FALL, 2009 Please answer problems 35, 39, 48, 54 and 61 in Chapter 8 of Bruice and the following questions: (1) Indicate how would you carry out the following chemical transformations by listing specific reagents, solvents, and conditions. CH 2 OH CH 2 SCH 3 H 3 C CH H 3 C OTs H 3 C CH H 3 C N 3 OH OCH 3 (a) (b) (c) (2) In the reaction scheme below, a stable intermediate A is formed when the starting chloroalcohol is reacted with base. Intermediate A is then transformed into two different products B and C upon exposure to HBr. Propose a structure for A and a reaction mechanism leading to its formation. Also propose
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Unformatted text preview: mechanisms by which A forms B and C . Your mechanism should explain the fact that two stereocenters in B are mixtures of stereoisomers, but that the stereochemistry of C is well-defined. CH 3 CH 3 Cl OH CH 3 Br CH 3 OH NaOH A HBr + CH 3 CH 3 OH Br B C (3) Classify the following solvents, which are used occasionally in organic chemistry, as protic or aprotic, polar or nonpolar, and donor or nondonor: (a) carbon disulfide: S=C=S (b) 2,2,2-trifluoroethanol: CF 3 CH 2 OH (c) nitrobenzene, C 6 H 5 NO 2 (d) 1,2-dimethoxyethane: CH 3 OCH 2 CH 2 OCH 3...
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