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Need help finding structure for H NMR

Need help finding structure for H NMR-example-1
User Glibdud
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1 Answer

3 votes

Answer:

Ethoxybenzene

Step-by-step explanation:

1. Index of hydrogen deficiency

Formula = C₈H₁₀O

Saturated = C₈H₁₈

IHD = (18 - 10)/2 = 8/2 = 4

The compound contains four rings and/or double bonds.

Whenever IHD ≥ 4, I immediately think of a benzene ring. That immediately accounts for all four units of unsaturation (1 ring + 3 double bonds).

There are 5H in the aromatic region (δ = 7.0 - 7.4), so I suspect a phenyl group.

The rest of the molecule must be saturated.

2. Triplet-quartet

The 3H:2H triplet-quartet is the classic signature of an ethyl group.

3. Structure

The only atom left is the O atom, and it must go between the ethyl and the phenyl group.

The compound is ethoxybenzene.

4. Confirmatory evidence

The CH₂ group is quite far downfield. The normal range for RCH₂-OR is δ = 3.5 - 3.9. I would expect RCH₂-OPh to be shifted even further downfield by the phenyl group.

The diagram below shows my interpretation of the spectrum.

Need help finding structure for H NMR-example-1
User Salviati
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