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  4. Lowest pKa is associated with Monobromination of 2-methylbutane gives how many distinct isomers?

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Q. Lowest $ pK_{a} $ is associated with Monobromination of $2$-methylbutane gives how many distinct isomers?

Delhi UMET/DPMTDelhi UMET/DPMT 2011

Solution:

Structure of $2$-methylbutane $CH_3 - \underset{\overset{|}{CH_3}}{CH} - CH_2 - CH_3$ Since there are four different types of hydrogen, thus four types of isomers are obtained.
$\underset{\text{1-bromo - 2- methylbutane}}{Br- CH_2 - \underset{\overset{|}{CH_3}}{CH} - CH_2 - CH_3} ; \underset{\text{2- bromo-2-methylbutane}}{CH_3- \underset{\overset{|}{CH_3}}{\overset{\underset{|}{Br}}{C}} - CH_2 - CH_3}$
$\underset{\text{2 - bromo - 3 - methylbutane}}{CH_3 - \underset{\overset{|}{C}H_3}{CH} - \overset{\underset{|}{B}r}{CH} - CH_3} ; \underset{\text{1 - bromo-3-methylbutane}}{CH_3 - \underset{\overset{|}{CH_3}}{CH} - CH_2 - CH_2 - Br}$