Chem 210-1F08 Qz4a

Chem 210-1F08 Qz4a - That is, if you assume a particular...

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Chemistry 210-1 Fall 2008 4th Quiz Consider the compounds below, which are divided into two families: reactants that are bases /nucleophiles, and substrates: r e a c t a n t s : H 3 C C O O H 3 C O N O O O CH 3 CH 2 OH H 3 C C CH 2 CH 3 CH 3 O ' A ' ' B ' ' C ' ' D ' ' E ' ' X ' ' Y ' ' Z ' s u b s t r a t e s : CH 2 CH 2 CH 2 Br Br CH 3 C D H CH 3 C CH 2 Br H 3 C H 1. Of the r e a c t a n t bases/nucleophiles, indicate those (if any) in which the r e a c t i v e s i t e is involved in electron delocalization. 2. What would be the effect of electron delocalization at such a reactive site on the reactivity of the compound as a nucleophile? (pick from one answer below): it would increase nucleophilicity it would decrease nucleophilicity no effect 3. Pick out the combination of one reactant and one substrate (of those listed above) which would give the fastest SN2 reaction. 4. Pick out the combination of one reactant and one substrate that would give the highest proportion of alkene product (relative to substitution product.
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Unformatted text preview: That is, if you assume a particular combination would give some alkene and some substitution product, for which combination will the ratio of alkene formed to substitution product formed be greatest? 5. Pick out the combination of one reactant and one substrate that would include in the product mixture a compound present as a racemic modification. 6. Provide a reaction (or series of reactions) which you could use to prepare compound 'X' from the starting material Ph-CH 2-CH 2-CH 2-OH ("Ph" = a phenyl group). 7. Provide the structure of the alcohol required to give compound "Z" if you used the same reaction route you just described in answer (6). 'A' and 'C' 'B' and 'X' 'E' and 'Z' 'D' and 'Z' 1) TsCl / pyridine; 2) NaBr / Dmso C CH 2 H H 3 C HO...
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