Easy things the Hard things for me

[JakeMUSC]

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Hey,

I dont understand how this compound, 3-Bromo 4 Chloro 5 Methyl hexane has 3 chiral centers.

------H--Br--Cl---CH3--H
CH3--C--C---C----C----C -H
-----H-- H---H----H----H

(can u visualize that?)

My review book says, Carbon 3, 4, and 5 are chiral centers.

I understand that why 3 and 4 are chiral, but why is carbon 5 chiral?

Its bonded to a methyl at top, a methyl on right, a H on bottom, and C to the left. Doesnt the fact that its bonded to 2 methyls mean that its not bonded to 4 different subsitiuents? Is this an error in my book?

 

[luder98]

Hey,

I dont understand how this compound, 3-Bromo 4 Chloro 5 Methyl hexane has 3 chiral centers.

------H--Br--Cl---CH3--H
CH3--C--C---C----C----C -H
-----H-- H---H----H----H

(can u visualize that?)

My review book says, Carbon 3, 4, and 5 are chiral centers.

I understand that why 3 and 4 are chiral, but why is carbon 5 chiral?

Its bonded to a methyl at top, a methyl on right, a H on bottom, and C to the left. Doesnt the fact that its bonded to 2 methyls mean that its not bonded to 4 different subsitiuents? Is this an error in my book?

You are correct. All four have to be different. Also the naming doesn't sound right to me. It should be 4-bromo-3-chloro-2-methylhexane (instead of 5-methyl), shouldn't it?

 

[calbear14]

You are correct. All four have to be different. Also the naming doesn't sound right to me. It should be 4-bromo-3-chloro-2-methylhexane (instead of 5-methyl), shouldn't it?

I thought that the substituents should be placed on the lowest numbered carbons as well.

 

[JakeMUSC]

I thought that the substituents should be placed on the lowest numbered carbons as well.

Yeah, I forgot to do that in the nomenclature. So there are only 2 chiral centers??

 

[calbear14]

So there are only 2 chiral centers??

Yep, luder98 is correct.