Asked Feb 20, 2020

The reaction of 2-ethyl-1-pentene with Br2, with H2 + Pd/C, or with R2BH/THF followed by aqueous HO- + H2O2 leads to a racemic mixture. Explain why a racemic mixture is obtained in each case.


Expert Answer

Step 1

In bromination reaction, bromine atom is introduced to a compound.

Hydrogenation can be done using the catalyst Pd/C results in the conversion of alkenes to alkanes. The addition will be a syn addition.

The hydroboration-oxidation reaction (BH3-THF, followed by treatment with a basic solution of hydrogen peroxide) takes place with syn stereochemistry. The resulting product has the hydroxyl group on the carbon with less number of alkyl substituents.

Step 2

The reactions are shown below,

Here, asymmetric centers are marked using asterisk.

Chemistry homework question answer, step 2, image 1


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