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A compound (C_9H_9BrO_2) gives the following NMR data. Draw the structure of the compound.
'1^H-NMR: 1.39 ppm, t(3H); 4.38 ppm, q(2H); 7.57 ppm, d(2H); 7.90 ppm, d(2H)
13^C-NMR: 165.73; 131.56; 131.01; 129.84; 127.81; 61.18; 14.18
You do not have to consider stereo chemistry.
You do not have to explicitly draw H atoms.
Do not include lone pairs in your answer.

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Answer:

ethyl 4-bromobenzoate

Explanation:

In this question, we can start with the Index of Hydrogen Deficiency (I.H.D):

[tex]I.H.D=\frac{2C+2+N-H-X}{2}=\frac{(2*9)+2+0-9-1}{2}~=~5[/tex]

This indicates, that we can have a benzene ring (I.H.D = 4) and a carbonyl group (I.H.D = 1), for a total of 5.

Additionally, in the 1H-NMR info, we have a triplet 1.39 (3H) followed by a doublet 4.38 (2H), this indicates the presence of an ethyl group ([tex]CH_3-CH_2-[/tex]). Also, in the formula, we have 2 oxygens if we have carbonyl group with 2 oxygens we have a high probability to have an ester group.

[tex]O=C-O-CH_2-CH_3[/tex]

Now, if we add this to the benzene ring and the "Br" atom that we have in the formula, we will have ethyl 4-bromobenzoate.

See figures 1 and 2 to further explanations.

I hope it helps!

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