Monochlorination of 2-methylbutane

[Xo1991]

Destroyer is saying that there are 6 stereoisomer products. I count five.

They are saying that 1-chloro-2-methylbutane is chiral, so it has an enantiomer. That molecule is not chiral, it is attached to two hydrogens and a carbon. Did destroyer make a mistake?

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[monsieurwise]

The C1 is not chiral, you are right
But C2 where the methyl is attached is chiral.

 

[Xo1991]

C-2 is not chiral. There are two methyl groups attached. Only C-3 is chiral: it is attached to a methyl, hydrogen, chlorine, and isopropyl.

I think destroyer made a mistake on this one? Odd because on the solutions it says "This is a tricky problem."

 

[patricklin27]

what problem is this?

 

[athomas]

C-2 is not chiral. There are two methyl groups attached. Only C-3 is chiral: it is attached to a methyl, hydrogen, chlorine, and isopropyl.

I think destroyer made a mistake on this one? Odd because on the solutions it says "This is a tricky problem."

If you draw out 1-chloro 2-methyl butane, it is chiral

the c2 is connected to c2h5 on one side (the C3 and C4 in butane) the methyl group, and the CH2Cl group on the other side (C1 and the chlorine)

Where are you getting that it is attached to two methyl groups?

 

[Xo1991]

Ahh, now I see. You're right. I was just looking at the carbon at which the Chlorine was attached to. I forgot to look at the rest of the molecule.

Tricky problem after all!

 

[elysium13]

I think monsieurwise was referring to C-2 being chiral in 1-chloro-2-methylbutane, which he is right. Prior to any chlorination, the C-2 in 2-methylbutane is not chiral, since like you said, it has two methyl groups.

 

[monsieurwise]

I think monsieurwise was referring to C-2 being chiral in 1-chloro-2-methylbutane, which he is right. Prior to any chlorination, the C-2 in 2-methylbutane is not chiral, since like you said, it has two methyl groups.

Uhm yes I was refering to 1-chloro-2-methylbutane. Thanks elysium13 =)