Destroyer Ochem Question

[egan]

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Number 33,

Consider the monochlorination of 2-methylbutane. How many products with stereoisomers counted?

I get 5, the answer says 6. There saying that there are two chiral centers, one of them being on the methyl of the 2-methylbutane. How can this be though as there are two hydrogens also attached to that carbon(making it achiral). Anyone know how this is chiral? Thankssss

 

[Bis-GMA111]

bump. would like to know this as well.

i see what you mean egan

 

[mh0000]

Number 33,

Consider the monochlorination of 2-methylbutane. How many products with stereoisomers counted?

I get 5, the answer says 6. There saying that there are two chiral centers, one of them being on the methyl of the 2-methylbutane. How can this be though as there are two hydrogens also attached to that carbon(making it achiral). Anyone know how this is chiral? Thankssss

After chlorinating the C1 carbon, C2 becomes chiral. YOu have a methyl group, hydrogen and a chloromethyl group on C2. The actual formation of the enantiomers depends on which of the methyl groups is chlorinated (which are initially equivalent)

 

[PooyaH]

You shouldn't look at the carbon where the Cl is attached to (C#1). In 1-chloro-2-methylbutane, carbon #2 is chiral.

 

[FROGGBUSTER]

This one is really tricky. If you look at both I & III in the solutions, you'll see that there is a chiral carbon in each.

For I, the chiral carbon is at the 2 position (the carbon attached to the methyl), and for III, the chiral carbon is at the 2 position as well (the carbon attached to the Chlorine).

I think almost everyone would get this one wrong if it was on the DAT, lol.

 

[radmazindds]

Look at structure I in the answer key of that problem. C2 from the LEFT has four different groups attached to it: a hydrogen, a methyl chloride (not sure that's exactly what it's called), a methyl, and an ethyl. This is chiral center #1. Therefore, we count this structure PLUS its enantiomer. (That's two so far)

Now look at structure III in the answer key:
C2 from the RIGHT has four different groups attached to it once again: a methyl group, an isopropyl group, a hydrogen, and a chlorine. that's a chiral center. It and its enantiamer makes two more--so, four so far.

Plus Structure II, plus structure IV. That makes six.

Hope that helped. 🙂

It's tricky, don't forget ur H's!

Number 33,

Consider the monochlorination of 2-methylbutane. How many products with stereoisomers counted?

I get 5, the answer says 6. There saying that there are two chiral centers, one of them being on the methyl of the 2-methylbutane. How can this be though as there are two hydrogens also attached to that carbon(making it achiral). Anyone know how this is chiral? Thankssss