[brandon78]

So far I think I have 5 carbons and a bromine looking like this.
http://imgur.com/65AZJdo

  But that does not match up to the H NMR simulations I found here.
http://web.chemdoodle.com/demos/simulate-nmr-and-ms


Here are the mass spec, infrared spec, C NMR, and H NMR.
http://imgur.com/a/tGks7#0

Any help would be appreciated.

[Archer]

Scrap the first molecule, that does not exist.

Start with the NMR.

How many different chemical environments are there?

What is the splitting on each of the 1H NMR, what does that tell you about the neighbouring groups.

[Archer]

The integrals for the ¹H NMR are wrong. You only have to look at the peaks at δ 1.3 ppm and δ 1.8 ppm to see they are non equivalent in area. The peak at δ1.3 ppm is smaller than the one at δ1.8 ppm.

Try using the ratio 2:2:1 and see if that helps, this is backed up by the relative peak heights in the ¹³C NMR.

[brandon78]

I think I'm getting C₅H₁₀Br₂.

The structure would be a long carbon chain with the Br on each end.

[Archer]

I think I'm getting C₅H₁₀Br₂.

The structure would be a long carbon chain with the Br on each end.

That's what I believe it is, 1,5-dibromopentane. It is similar to 1,6-dibromohexane in the other spectral data, which would give the 1:1:1 ratio, however this does not match the MS data.

http://webbook.nist.gov/cgi/cbook.cgi?ID=C111240&Mask=200#Mass-Spec

http://webbook.nist.gov/cgi/cbook.cgi?ID=C629038&Mask=200#Mass-Spec