10.8k views
5 votes
What is the configuration of the product in the base-catalyzed hydrolysis of (R)-1-choloro-1-deuteriobutane?

User Nanotek
by
7.8k points

1 Answer

4 votes

Final answer:

In base-catalyzed hydrolysis of (R)-1-choloro-1-deuteriobutane, the product will have an (S)-configuration due to the backside attack by the nucleophile, characteristic of an SN2 reaction mechanism.

Step-by-step explanation:

The configuration of the product in the base-catalyzed hydrolysis of an alkyl halide such as (R)-1-choloro-1-deuteriobutane will be of the opposite configuration to the starting material, assuming the reaction proceeds via an SN2 mechanism. This mechanism involves a backside attack by the nucleophile (water in the case of hydrolysis), displacing the leaving group (chloride in this case) and inverting the configuration of the stereocenter.

For example, in the base-catalyzed hydrolysis of (R)-1-choloro-1-deuteriobutane, the carbon attached to the chlorine will be attacked from the back side by a hydroxide ion (OH-) in a concerted process. As a result, the product will have an (S)-configuration at the carbon that was originally attached to the chlorine. This inversion of configuration is characteristic of the SN2 reaction pathway.

It's worth noting that the stereochemical outcome of a reaction is important in synthetic chemistry, as it can affect the biological activity and properties of molecules.

User Bahri Noredine
by
8.2k points