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Topic: Overlapping signal sets on HNMR  (Read 802 times)

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Offline annalgam

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Overlapping signal sets on HNMR
« on: November 27, 2020, 03:05:42 PM »
I've spent the past day trying to figure out the structure for the given formula C6H12O from the given HNMR and for the life of me, I don't know if I'm doing something wrong or I just don't have a deep grasp of HNMR, but I can't figure out the structure. I think it's mainly the overlapped set that's confusing me. I read online somewhere that the 3H overlap could be a CH2 overlapping CH or OH but I didn't learn anything like that so I'm uncertain about this, so if anyone could explain what this means, I'd really appreciate it. Thanks.

What I have so far:


There should be a double bond in there somewhere since the IHD is 1.

The 3H set around 1 should be a -CH2-CH3

The 3H set around 1.5 should be -CH3 with 1 neighboring H so either a -CH(-C)-CH3 with no H's on the (-C) or -CH=CH3.

The 1H set around 3.3 should be a CH with 3 H neighbors and alpha to O atom so CH3-CH(-C)-O- with CH's fourth substituent being a C with no H's or it could be -CH2-CH(-CH)-O- maybe?

The 2H set around 2ppm is either a quartet or a pentet with an overlapping 3H singlet? I'm already confused about it overlapping so I hope someone could explain what this could mean.

The closest I've gotten was
C-C=C(-O-C-C)-C but there's a vinylic H in there so that's clearly not it...
« Last Edit: November 27, 2020, 03:31:18 PM by annalgam »

Offline AWK

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Re: Overlapping signal sets on HNMR
« Reply #1 on: November 28, 2020, 06:41:32 AM »
IHD (index of hydrogen deficiency) informs you about the possible presence of double bonds or rings. In the case of your compound, double bonds can form C with C or O.
The NMR spectrum is computer-simulated with poor resolution and the smallest peaks from the weaker multiplets may not be visible. The compound in no way contains the double bond C = C.
« Last Edit: November 28, 2020, 08:17:02 AM by AWK »
AWK

Offline rolnor

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Re: Overlapping signal sets on HNMR
« Reply #2 on: November 28, 2020, 09:54:04 AM »
What about a ketone?

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