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What chemical gives this NMR sequence?

http://aceorganic.pearsoncmg.com/epoch-plugin/temp...

I'm positive it has an aromatic ring and im MOSTLY sure that it has 12 H and an ether/alcohol group, but i could be wrong on the latter part.

Update:

ok, so it definitely only has 8 H and im not positive it has an aromatic ring. I was blissfully ignorant and adherent to the N+1 rule

1 Answer

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  • Cubbi
    Lv 7
    1 decade ago
    Favorite Answer

    No aromatic ring here unless it is entirely substituted by non-hydrogens.

    And yes, N+1 rule is perfectly usable here. Also keep an eye on integrations: you have 2H, 1H, 2H, and 3H.

    The 3H at 0.92 ppm is a very typical -CH3

    It shows up as a triplet, meaning the next carbon has two hydrogens.

    The 2H at 1.56 ppm shows up as a sextet, so it sees the three protons of the -CH3 and two more. Meaning this CH2 is connected to another CH2

    The 2H at 3.56 ppm is a quartet, meaning it sees the two protons of the middle CH2 and one proton elsewhere.

    The 1H at 3.2 ppm is a triplet which means it's sees that last CH2 and nothing else.

    Thus, CH3-CH2-CH2-CHXY?

    However, look at the chemical shift of the last CH2. 3.5 is typical of a carbon attached to an oxygen. There's no way a substituent on the CH could pull CH2 further to the left than the CH.

    So this is simply 1-propanol: CH3-CH2-CH2-OH

    database chemical shifts: 0.94 ppm, 1.57 ppm, 3.58 ppm. The shift of the -OH can vary depending on the solvent, but typically comes up between 2 and 4 ppm. It is rare to see coupling between hydroxyl proton and alpha-carbon's proton, but looks like your solvent did not exchange the OH at all, so it makes sense.

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