Question

The deuterated ethanol below can be converted to an alkyl halide via a tosylate intermediate. Complete the mechanism, draw the final product (with nonbonding electrons) and select the correct absolute stereochemistry of the starting material and the final product.Draw curved arrows.

Answer 1

Answer:

See explanation below

Explanation:

Picture 1 show the original starting material. Picture 2, shows the mechanism involved to get the final product. This is a reaction with sustitution. So, the first step is the nucleophylic attack of the OH of the ethanol to the tosylate. This means that the chlorine goes out. When this happens, the chlorine becames in the next step a nucleophyle, so it attacks to the carbon of the ethane tosylate intermediate. As tosylate is a very good outgoing group, this goes out of the molecule and then, the alkyl halide is formed.

As for the stereochemistry, if the initial reactant has a S configuration, then the final product will be R, and if it's R, then the final would be S. See picture for mechanism: