Problem 5- Dialkylcuprate Additions Cu Li O

1. 2. H2O

1. How many conjugated p-orbitals are there in the starting material? How many in the product?

2. Indicate the bond dipoles present in the lithium-copper reagent used in this reaction. Cu Li 3. This reagent acts as a nucleophile in this reaction. Draw the products of the reaction shown below. Hint: The lithium breaks its ionic interaction with copper and forms a new ionic interaction.

O Li Cu Intermediate 4. The water is used as an acid to give the nal product. Use curved arrows to propose a mechanism for product formation from the intermediate you drew above.

Intermediate 5. Construct six Newman projects to show the relative energy levels of the product as the bond shown in bold is rotated in 60 degree increments. Plot the energies on a graph.

Relative Energy

Degrees of Rotation

Created by Hanna Key Grinnell College

6. Suppose this cuprate-lithium reagent is used in this reaction instead. Draw the product of the reaction.

6. Suppose this cuprate-lithium reagent is used in this reaction instead. Draw the product of the reaction.

1. 2. H2O

Cu Li

7. Construct six Newman projects to show the relative energy levels of the product as the same bond as in the previous product is rotated in 60 degree increments.

8. Onto the axes below, copy your plot from the original product. Then, plot the relative energies of the six conformations of the new product. In each case, decide whether the original or new product would be more highly strained.

Relative Energy

Degrees of Rotation 9. For the following possible products of this reaction type, determine the longest carbon chain and provide a name for the circled branched substituent.

O O O