How to find possible unique monochlorinated isomers?

write the number of unique mono chlorinated isomers including stereoisomers of 2-methylpentane

1 Answer
anor277
Apr 19, 2018

We start with achiral #underbrace(H_3C-CH(CH_3)CH_2CH_2CH_3)_"2-methylpentane"#

Explanation:

And so we substitute the chain with #X#...and get...

#H_2XC-stackrel2CH(CH_3)CH_2CH_2CH_3#, #"1-halo-2-methylpentane"#, and this will generate a pair of enantiomers...#C2# is now stereogenic.

#H_3C-CX(CH_3)CH_2CH_2CH_3#, #"2-halo-2-methylpentane"#, and this will generate NO enantiomers...#C2# is no longer stereogenic because of symmetric dimethyl substitution.

#H_3C-CH(CH_3)CHXCH_2CH_3#, #"3-halo-2-methylpentane"#, and this will generate ONE pair of enantiomers ....

And #H_3C-CH(CH_3)CH_2CHXCH_3#, #"2-halo-4-methylpentane"#, and this will generate ONE pairs of enantiomers ... carbons 2 is potentially chiral...

And lastly, #H_3C-CH(CH_3)CH_2CH_2CH_2X#, #"1-halo-4-methylpentane"#, and this will generate NO enantiomers ....

Have I got them all?

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