Chem 220a                                          Problem Set 8                                     Fall  2003

 

 

 

1.   How would you carry out the following transformations? More than one step may be needed.

 

 

 

  1. Propose a synthesis of muscalure, the sex attractant of the common housefly, starting from acetylene and any alkyl halides.

 

 

 

 

 

 

 

  1. Hydrocarbon A has the formula C12H8.  It absorbs 8 equivalents of hydrogen upon catalytic reduction using a palladium catalyst.  Upon ozonolysis only two products are formed: oxalic acid (HOOC-COOH) and succinic acid (HOOCCH2CH2COOH).  What is A?  Explain concisely.

 

 

4.   Compounds B and C have the formula C7H14.  They are optically inactive; they are not resolvable, and they are diastereomers of each other.  Catalytic hydrogenation of B or C yields D.  D is optically inactive, but it could be resolved into separate enantiomers. Identify B, C, and D. Explain concisely.