Q16 of 37 Page 1

Following compounds are given to you :

2-Bromopentane, 2-Bromo-2-methy-lbutane, 1-Bromopentane


(i) Write the compound which is most reactive towards reaction.


(ii) Write the compound which is optically active.


(iii) Write the compound which is most reactive towards β–elimination reaction.

(i)

















1- bromo – pentane – contains primary carbon





2-bromo – pentane – contains secondary carbon





2-bromo-2-methyl-butane – contains tertiary carbon



Formation of the transition state is involved in sn2 reactions. More is the stability of transition state, more is the reactivity towards sn2 reactions. Lesser the steric hindrance due to surrounding groups more is the stability. Wen can observe that 2-bromo-2-methyl-butane has most steric hindrance followed by 2-bromo – pentane and then by 1-bromo-pentane. So, reactivity towards sn2 reactions is


1-bromo-pentane > 2-bromo – pentane > 2-bromo-2-methyl-butane


(ii) 2-bromo-pentane is optically active since it has chiral carbon i.e. the carbon attached to 4 different groups or atoms.


(iii) 2-bromo-2-methylbutane is most reactive towards β-elimination reaction because here more substituted alkene is the major product.



2-bromo-2-methylbutane 2-methyl-but-2-ene


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