Name: ___________________________               

	           


EXAM 4
CHEMISTRY 220a
Friday, December 8, 2000

NAME (print): ___________________________________________________

TA:_____________________    Day:_________________ Time:__________


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

Write your name on the top of each page where indicated.

Important items are in bold.

A Periodic Table is on page 9.   

Do all preliminary drawing or computations on the work sheets (pgs. 6-8). The work sheets 
will not be graded.

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. (25 pts)	______


2.  (23 pts)	______


3.  (24 pts)	______


4.  (28 pts)	______

_______________________________

Total (100 pts)  

1)  	(5 x 5 pts. = 25 pts.)  Provide the products in each of the following reactions.  Pay 
attention to stereochemistry where applicable.
                                                   

2)  	(23 pts.)  Design a synthesis of 3-hexanone using 1-propene as the only source of carbon.  
No acetylene chemistry.  All reagents are available to you.

3)  	(24 pts.)  Compound A (C7H14) reacts with cat. OsO4/HIO4 to form B (C3H6O) and C.  
Compound B does not react with PCC (pyridinium chlorochromate) in CH2Cl2 as solvent.  
When water is added to this reaction mixture, D (C3H6O2) is formed.  Compound C does not 
react with PCC or K2Cr2O7/aqueous H2SO4. What are the structures of A-D? Explain.  What 
limitation is placed on your answer?

4)    (7 x 4 pts. = 28 pts.)  Provide the reagents necessary to complete the reaction sequences A-G.  
Some transformations require more than one step.  All C1 carbon sources and reagents are 
available to you.  Transformation D is a reaction from Chapter 11. 

                                           

A:


B:


C:


D:


E:


F:


G:

		Work Sheets

	Work Sheets

	Work Sheets

	Periodic Table