The structure of D-isoleucine (a variant of L-isoleucine) is shown below. Its co

Question

The structure of D-isoleucine (a variant of L-isoleucine) is shown below. Its configuration is 2R, 3R and its optical activity [a_D] = -12.4 degree. - assign the configuration of the enantiomer - give the optical activity of the enantiomer - assign the configurations of the two diastereomers A student proposes to synthesize the compound shown below by nitration of benzene with nitric acid followed by alkylation with methyl chloride. What's wrong with this approach? What should the student do instead?

Explanation / Answer

12) For the given compound,

Configuration of enantiomer L-Isoleucine = R,R

Optical activity of enantiomer = +12.4 degree

Configuration of diastereomer : Ist - R,S and IInd - S,R

13) Nitro- group is electron witdraing in nature and results in meta- substitution on benzene ring. So nitrobenzene would yield a meta-acylated product instead of required para-product.

Instead, the student should alkylated benzene with CH3Cl and AlCl3 first and then do nitration to form the required product.

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