Organic Chemistry 1 Test

Question 1:

Fill the boxes with the products obtained or the reagents needed. Make sure to include the correct

stereochemistry where it is needed. (2 points each) 20 pts

 

 

 

 

 

 

A= E=

 

 

B-= F=

 

 

 

 

C= G=

 

 

 

D= H=

 

 

 

 

 

 

Which one of the following molecules is susceptible to autooxidation faster? Explain your

choice by drawing the corresponding free radical intermediate. 4 pts)

 

 

 

 

 

 

 

 

Question 2

Identify the intermediate molecules A, B and C for the following transformations. 6 pts

 

 

 

 

 

C= B= A =

 

 

 

 

Devise a method to prepare 3-bromo-1-propanol from 2-bromopropane. 6 pts

(No mechanism needed, only draw the reagents and intermediate molecules)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Question 3:

Predict the product(s) including stereochemistry and propose a mechanism for the following reaction:

(draw only initiation and propagation steps) 9 pts

 

 

 

 

 

 

 

 

 

 

MECHANISM:

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

An unknown compound, A, has the molecular formula C8H14. Catalytic hydrogenation of A with H2/Pt

yields a product with the molecular formula C8H18 (B). Upon ozonolysis (O3, H2O) A gives one product C.

What are the structures of A, B and C? (show your work) 6 pts

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Predict the products (include stereochemistry) when following compound is treated with NBS and

irradiated with UV light. If Br2 and light had been used, what competing reaction would have occurred

(list the products of that reaction too).

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

Extra Credit: Propose a mechanism for the following reaction. 5 pts