EXAM 4

CHEMISTRY 220a

Friday, December 6, 2002

 

NAME (print): ___________________________________________________

 

TA:_____________________    Day:_________________ Time:__________

 

 

Take a few moments to look over the exam.  Answer each question on the exam paper.

 

Important clues, points, and structures are in bold.

 

 Do all preliminary drawing or computations on the work sheets at the end of the exam. The work sheets will not be graded

 

There  is a Periodic Table on the last page of the exam.

 

The exam is 55 minutes.

 

STOP writing and hand in your exam when you are asked to do so.

 

Remember: Neatness is to your advantage.

 

1. Synthesis  (20 pts)              ______

 

 

2.  Reactions  (30 pts)             ______

 

 

3.  Structure (20 pts)               ______

 

 

4.  Potpourri (30 pts)              ______

 

 

_______________________________

 

Total (100 pts) 


1.   (20 pts) Synthesis: A chemist requires a sample 3-methyl-3-heptanol (1).  She designs and executes a synthesis of 1 using 1-butene as her sole source of carbon atoms.  She has access to all other reagents.

 

a) (15 pts) Show how you would accomplish this synthesis.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

              b) (5 pts)  Is compound 1 from the synthesis optically active or not? Explain briefly.
2.  (30 pts) Reactions: Provide the expected product(s) of the following reactions.  Pay attention to stereochemistry.

 

 

3.   (20 pts) Structure:  Given the reactions shown below,

 

 

 

      a) (10 pts) What are the structures of A and B? Explain and illustrate.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

      b) (10 pts) Show how C and D are formed from B.

4. (30 pts) Potpourri:  Provide answers for the following  questions.  Circle  your answers in all but #2.

 

 

a) How many stereoisomers of the tetramer of acetaldehyde (1)  are possible?

 

 

 

 

 

 

b)  The remaining steps needed to convert alkene 1 into its geometrical isomer 2.

 

    

 

 

 

 

c)  Functional groups that are unreactive toward a Grignard reagent

 

 

 RCOOH               ROH                ester                alkene              ether

 

 

 

 

 

d)  The major by-product in the oxidation of a primary alcohol to an aldehyde  with PCC

under anhydrous conditions

 

 

ester           carboxylic acid            ether                ketone              amide

 

 

 

 

 

e)  The compound not at the same oxidation level as the other four

 

 

Work Sheets

Work Sheets


Work Sheets

Periodic Table