Simple nomenclature question

[SailCrazy]

Please check out the question below.
I thought this would be 2-Cholro-4,4-dimethylhexane?
What am I missing?


The systematic name for the compound (CH3)2C(CH2.CH3).CH2.CHCl.CH3 is:

Correct Answer: 5-chloro-3,3-dimethylhexane

Feedback:

On Test Day, you may be asked to determine the IUPAC name of a compound such as the one in the question stem. The best way to handle this type of question is to start by drawing the molecule to be named. That is, translate

(CH3)2C(CH2.CH3).CH2.CHCl.CH3
into:

[molecule picture was here]

Now, use the nomenclature rules to determine the IUPAC name of this compound.

The longest carbon chain containing the principal functional group is 6 carbons long (hexane). The substituents include a chloro group and two methyl groups. Putting it all together gives 5-chloro-3,3-dimethylhexane. Choice (A) is correct.

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[GoBlue129]

you're right. 2-chloro-4,4-dimethylhexane.

 

[SailCrazy]

Stupid KAPLAN wrong answer! I was really confused there for a while...

you're right. 2-chloro-4,4-dimethylhexane.

 

[QofQuimica]

You should number the carbon atoms from the side nearer to the first substituent, which is chlorine if I'm reading your molecule correctly. The molecule would be 2-chloro-4,4-dimethylhexane as you said. Where did this problem come from, sailcrazy? I'll report it to the powers that be.

 

[SailCrazy]

This question was from the online "Nomenclature & Functional Groups Quiz". It is a part of the "Before Session 6:Organic Chemistry 1" assignments.

There are a few subtleties of the naming rules that I don’t know, and I was afraid that this question was testing one of them!

Thanks for the help.

You should number the carbon atoms from the side nearer to the first substituent, which is chlorine if I'm reading your molecule correctly. The molecule would be 2-chloro-4,4-dimethylhexane as you said. Where did this problem come from, sailcrazy? I'll report it to the powers that be.

 

[QofQuimica]

This question was from the online "Nomenclature & Functional Groups Quiz". It is a part of the "Before Session 6:Organic Chemistry 1" assignments.

There are a few subtleties of the naming rules that I don’t know, and I was afraid that this question was testing one of them!

Thanks for the help.

Ah, the online workshop. I should have known. I already reported several mistakes in the organic workshops last year; I read through all of the slides while I was studying just to check them out. Maybe I missed that one, but anyway, I'll let them know. Good job catching it.