The number of possible organobromine compound | vedclass

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(D) $NBS$ $(N-bromosuccinimide)$ performs allylic bromination via a free radical mechanism. For $but-1-ene$ $(CH_3-CH_2-CH=CH_2)$, the allylic hydroge

Vedclass · Accepted Answer

$4$

Vedclass · Answer

(D) $NBS$ $(N-bromosuccinimide)$ performs allylic bromination via a free radical mechanism. For $but-1-ene$ $(CH_3-CH_2-CH=CH_2)$, the allylic hydrogen is at the $C-3$ position. Abstraction of this hydrogen generates an allylic radical: $CH_3-\dot{C}H-CH=CH_2 \leftrightarrow CH_3-CH=CH-\dot{C}H_2$. Reaction of this resonance-stabilized radical with $Br \cdot$ leads to two constitutional isomers: $1$. $3-bromobut-1-ene$ $(CH_3-CH(Br)-CH=CH_2)$, which contains a chiral center and thus exists as a pair of enantiomers ($d$ and $l$). $2$. $1-bromobut-2-ene$ $(CH_3-CH=CH-CH_2Br)$, which exhibits geometrical isomerism ($cis$ and $trans$). Therefore, the total number of possible organobromine compounds is $2$ (enantiomers)   $2$ (geometrical isomers) = $4$.

The number of possible organobromine compounds which can be obtained in the allylic bromination of $but-1-ene$ with $N-bromosuccinimide$ $(NBS)$ is

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