Epoxidation (Meeting 8)

Problems Set #8

ATTN: answers to the below questions are due at the start of your lab period of Meeting 8; these answers should be part of your pre-lab write-up.

1. Using the ACSlab software, simulate the ¹H-NMR and the ¹³C-NMR spectrum for 4-chlorostyrene, its epoxide and 4-chlorobenzacetaldehye (Cl-C₆H₄-CH₂CHO). Answer the following questions:

a. Which coupling pattern do the protons for the alkene show?. What are the coupling constants?

b. Which coupling pattern do the protons the epoxide ring show? What are the coupling constants?

c. Which coupling pattern do the protons for the CH₂ group and the aldehyde show? What are the coupling constants?

d. How can you distinguish between the aldehyde and the epoxide using C-NMR spectroscopy?

2. On a polar TLC plate, which of the three compounds would move the farthest up the TLC plate, which one the least?