The maximum no. of isomers (including stereoisomers) that are possible on mono-chlorination of the compound: 3,3-dimethylpentane is? The answer given is 5.

My working: The fourth carbon is chiral when chlorine is added to it, so it'd have an enantiomer, and there are two other carbons where chlorine can be substituted, so how is the answer 5?

  • $\ce{CH3-CH2-C(CH3)2-CH2-CH2Cl}$,
  • $\ce{CH3-CHCl-C(CH3)2-CH2-CH3}$ (this is chiral and would have an enantiomer),
  • $\ce{CH3-CH2-C(CH2Cl)(CH3)-CH2CH3}$

are the compounds I could make out.

  • $\begingroup$ Can you show us the structures you have come up with? $\endgroup$ – Michael Lautman May 22 '19 at 16:59
  • $\begingroup$ 2 is same as 4 so one less. $\endgroup$ – Mithoron May 22 '19 at 17:08
  • $\begingroup$ @MichaelLautman I've edited the question. Please see if it answers your question. $\endgroup$ – Tapi May 22 '19 at 17:13
  • 2
    $\begingroup$ Who said the answer was five? You've got it all right. $\endgroup$ – Karl May 22 '19 at 17:28

enter image description here

only 4 products are are formed.

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