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Question 57


Consider the above chemical reaction. The total number of stereoisomers possible for Product "P" is _________


Correct Answer: 2

The starting alkene is:

$$\mathrm{cis\text{-}2\text{-}butene}$$

The reaction involves bromination:

$$\mathrm{Br_2/CCl_4}$$

Addition of bromine occurs through formation of a cyclic bromonium ion intermediate.

Hence, the reaction proceeds via:

$$\mathrm{anti\text{-}addition}$$

Stereochemical outcomes of anti-addition:

$$\mathrm{cis\text{-}alkene \rightarrow Racemic\ Mixture}$$

$$\mathrm{trans\text{-}alkene \rightarrow meso\ Compound}$$

Since the starting alkene is:

$$\mathrm{cis\text{-}2\text{-}butene}$$

the product formed is a racemic mixture of:

$$\mathrm{(2R,3R)\text{-}2,3\text{-}dibromobutane}$$

and

$$\mathrm{(2S,3S)\text{-}2,3\text{-}dibromobutane}$$

Thus, total stereoisomers formed:

$$\mathrm{= 2}$$

Final answer:

$$\mathrm{2}$$

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