CHEM%210% [CHAPTER%6: SUBSTITUTION REACTIONSOF ALKYL HALIDESchemistry.bd.psu.edu/justik/CHEM 210/CHEM 210 CH 09 Addition... · Addition’Reactionsof’Alkenes’!...

CHEM  210   [CHAPTER  6:  SUBSTITUTION  REACTIONS  OF  ALKYL  HALIDES    

    1   Fall  2013    

Addition  Reactions  of  Alkenes  

Our  text  does  not  cover  reaction  8  until  a  later  chapter  

Additional  Problems    

1. Predict  the  products  for  the  following  reactions:  

2. Propose  a  mechanism  for  the  following:  

CHEM  210   [CHAPTER  6:  SUBSTITUTION  REACTIONS  OF  ALKYL  HALIDES    

    2   Fall  2013    

3. Draw  a  mechanism  for  the  following:  

 4. If  an  alcohol  is  used  instead  of  water,  ethers  are  produced.    Draw  a  mechanism  for  the  following:  

5. Many  reactions  are  intramolecular.    Here  the  reactants  are  both  in  the  same  molecule.    Draw  a  mechanism  to  explain  the  following:  

 6. Mercury   is   toxic   and   used   only   when   necessary   for   synthesis.     In   class   we   learned   that   the   oxy-­‐

mercuration/demercuration  scheme  could  be  used  to  give  products  of  alkene  hydration  without  rearrangements.    For  each  of  the  following  reactions,  give  the  product  of  each  and  indicate  the  product  you  would  obtain  by  simple  hydration  in  aqueous  acid.  

7. Complete  the  following  examples  of  hydroboration/oxidation:  

CHEM  210   [CHAPTER  6:  SUBSTITUTION  REACTIONS  OF  ALKYL  HALIDES    

    3   Fall  2013    

8.  Complete  the  following  examples  of  hydroboration/oxidation.    Indicate  proper  stereochemistry  of  products.  

9. Predict  the  products  of  the  following  catalytic  hydrogenations.  

 10. Predict  the  products  of  the  following  halogenation  reactions:  

11. Predict  the  products  when  each  alkene  is  treated  with  a  mixture  of  water  and  Br2:  

 12. Bromonium  ions  can  be  captured  by  nucleophiles  other  than  water.    Predict  the  products  of  the  following:  

13. Predict  the  products;  indicate  proper  stereochemistry  where  necessary:  

CHEM  210   [CHAPTER  6:  SUBSTITUTION  REACTIONS  OF  ALKYL  HALIDES    

    4   Fall  2013    

14. Predict  the  products  when  each  alkene  is  treated  with  O3  followed  by  Me2S:  

 15. Predict  the  products:  

 16. Predict  the  products:  

CHEM  210   [CHAPTER  6:  SUBSTITUTION  REACTIONS  OF  ALKYL  HALIDES    

    5   Fall  2013    

KEY  1. Predict  the  products  for  the  following  reactions:  

2. Propose  a  mechanism  for  the  following:  

 3. Draw  a  mechanism  for  the  following:  

 4.  

CHEM  210   [CHAPTER  6:  SUBSTITUTION  REACTIONS  OF  ALKYL  HALIDES    

    6   Fall  2013    

5.  

 6.    

 7.    

CHEM  210   [CHAPTER  6:  SUBSTITUTION  REACTIONS  OF  ALKYL  HALIDES    

    7   Fall  2013    

8.    

 9.    

CHEM  210   [CHAPTER  6:  SUBSTITUTION  REACTIONS  OF  ALKYL  HALIDES    

    8   Fall  2013    

10.    

 11.    

 12.    

CHEM  210   [CHAPTER  6:  SUBSTITUTION  REACTIONS  OF  ALKYL  HALIDES    

    9   Fall  2013    

13.    

CHEM  210   [CHAPTER  6:  SUBSTITUTION  REACTIONS  OF  ALKYL  HALIDES    

    10   Fall  2013    

14.    

 15.    

CHEM  210   [CHAPTER  6:  SUBSTITUTION  REACTIONS  OF  ALKYL  HALIDES    

    11   Fall  2013    

16.