NMR help

[tiny529]

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Hi!

I've got a problem here that I'm having a lot of trouble with...

Below are the 1H and 13C NMR spectra of a dichloroalkane. Analyze the spectra and propose a structure consistent with the data. Provide a COGENT explanation outlining how you arrived at the proposed structure (the NMR's are at the bottom... It's problem #5).

My problem is that I can easily make a structure that matches one or the other spectra, but I can't seem to make one that matches both.

My best answer is 3,3-dichloro-2-methylpentane, but that still doesn't match what I think the C NMR peaks show.

 

[Telomeres]

Your structure seems right on, as for the C13 NMR, if you look closely there seems to be another additional peak at approximately 60ppm. In general when I look at a C13 NMR for an alkane I tend to only use it for the amount of carbons present to reinforce the structure given by the H-NMR. The only big inconsistency that worries me about the H-NMR is the obscure peak within what looks like the quartet making me think their might be another variant of a hydrogen present.