The maximum number of isomeric monochloro der | vedclass

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Question

(A) The structure of $2,2,5,5-$tetramethylhexane is $(CH_3)_3C-CH_2-CH_2-C(CH_3)_3$.To find the number of isomeric monochloro derivatives,we identify

Vedclass · Accepted Answer

$3$

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(A) The structure of $2,2,5,5-$tetramethylhexane is $(CH_3)_3C-CH_2-CH_2-C(CH_3)_3$.To find the number of isomeric monochloro derivatives,we identify the non-equivalent hydrogen atoms in the molecule.$1$. The $12$ methyl hydrogens at the ends are equivalent (type $a$). Replacing one gives $1-$chloro-$2,2,5,5-$tetramethylhexane.$2$. The $4$ methylene hydrogens in the middle are equivalent (type $b$). Replacing one gives $3-$chloro-$2,2,5,5-$tetramethylhexane.Since the molecule is symmetric,there are only $2$ distinct sets of equivalent hydrogen atoms.However,the $3-$chloro derivative has a chiral center at the $C-3$ position,leading to a pair of enantiomers $(d$ and $l$ forms).Therefore,the total number of isomeric monochloro derivatives is $1$ (from type $a$) $+ 2$ (enantiomers from type $b$) $= 3$.

The maximum number of isomeric monochloro derivatives which can be obtained from $2,2,5,5-$tetramethylhexane by chlorination is $..............$.

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