Chapter11_Jones - Study guide for Chapter 11 1 Addition reactions of alkenes All alkene reactions from Chapters 10 and 11 are summarized in the

Chapter11_Jones - Study guide for Chapter 11 1 Addition...

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1 Study guide for Chapter 11 1) Addition reactions of alkenes All alkene reactions from Chapters 10 and 11 are summarized in the following table: Reagent Final atoms added Intermediate Regiochem . Shift Know mechanism? 1. Alkyl halide (HX) H, X C+ Markov. possible YES 2. H 2 SO 4 /H 2 O H, OH C+ Markov. possible YES 3. H 2 SO 4 /ROH H, OR C+ Markov. possible YES 4. 1) BH 3 then 2) H 2 O 2 /NaOH H, OH borane (concerted) anti-Markov NO YES 5. H 2 /Pd/C or Pt/H 2 or Ni/H 2 H, H None (syn concerted) N/A NO NO 6. Halogens (X 2 ) X, X Bridged (stabilized C+) Markov. NO YES 7. X 2 + excess H 2 O X, OH Bridged (stabilized C+) Markov. NO YES 8. X 2 + excess HOR X, OR Bridged (stabilized C+) Markov. NO YES 9. X 2 + excess NaX X, X Bridged (stabilized C+) Markov. NO YES 10. 1) Hg(OAc) 2 , H 2 O 2) NaBH 4 H, OH Bridged (stabilized C+) Markov. NO Only first step 11. CH 3 CO 3 H in CH 3 CO 2 H O (epoxide) None (concerted) N/A NO YES 12. RN 2 with hv or heat CHR (cyclopropane) None (concerted) N/A NO YES 13. CHX 3 , NaO t Bu CX 2 (cyclopropane) None (concerted) N/A NO YES 12. 1) O 3 2) Zn/H 2 O or S(CH 3 ) 2 or H 2 /Pd O, O (two carbonyls) ozonide (concerted) N/A NO Only first step 13. 1) O 3 ; 2) H 2 O 2 O, O (two carboxylic acids) ozonide (concerted) N/A NO Only first step 14. KMnO 4 , H 2 O, NaOH OH, OH Vicinal diol metal diol (concerted) N/A NO Only first step 15. OsO 4 , H 2 O, Na 2 SO 3 OH, OH Vicinal diol metal diol (concerted) N/A NO Only first step You should be able to perform the following tasks for each reaction above: a) Indicate the product given the starting compound and reagent. Be sure to be able to rationalize regioselectivity and stereoselectivity using carbocation/radical intermediates. b) Indicate the reagents needed given starting material and product. c) Indicate the starting material needed given reagents and product. d) Indicate how you might synthesize a product by indicating starting compound and reagents.
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