Draw the major product that is obtained when (2S,3S)-2-Bromo-3-phenylbutane is treated with sodium ethoxide, and explain the stereochemical outcome of this reaction.

Respuesta :

Neetoo

Answer:

(2S,3S)-2-Bromo-3-phenylbutane + C₂H₅ONa → E-2-phenyl-2-butene + NaBr + C₂H₅OH

C₁₀H₁₃Br + C₂H₅ONa → ‎C₁₀H₁₂ + NaBr + C₂H₅OH

Explanation:

When we add sodium ethoxide in solvent its ionic character increases Na⁺ ⁻OCH2CH3.

Upon adding (2S,3S)-2-Bromo-3-phenylbutane in the solution, Oxygen (O⁻) take the proton from position 3 of the 2-Bromo-3-phenylbutane. By extracting this proton the electrons at carbon 3 make bond with the carbon 2 having the bromine atom.

As bromine is a good leaving group so it easily get detached from carbon 2 making a double bond between carbon 2 and 3.

Stereo-chemical outcome

As a result of this elimination reaction E-2-phenyl-2-butene produces.

Why we call it as E

As we can see in the attached structure that both preority groups are in the same side or we can say that they are cis to each other.

When both priority groups are on same side or cis to each othe we call it as E if they are opposite or trans we call call them Z.

How to select priority groups

We select the priority groups by their atomic number. We give higher priority to that group which has higher atomic number.

Ver imagen Neetoo
Q&A Education