Draw the NMR spectra you expect for the following compounds.
(b)

An unknown compound has the molecular formula C₉H₁₁Br. Its proton NMR spectrum shows the following absorptions:

singlet, δ7.1, integral 44 mm

singlet, δ2.3, integral 130 mm

singlet, δ2.2, integral 67 mm

Propose a structure for this compound.

Five proton NMR spectra are given here, together with molecular formulas. In each case, propose a structure that is consistent with the spectrum.

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Give the spectral assignments for the protons in isobutyl alcohol (Solved Problem 13-4). For example, H^a is a singlet, area = 1, at δ2.4.

Propose chemical structures consistent with the following NMR spectra and molecular formulas. In spectrum (a), explain why the peaks around δ1.65 and δ3.75 are not clean multiplets, but show complex splitting.

(a) <IMAGE>

Draw the NMR spectra you expect for the following compounds.

(a)

Identify each of the following compounds from its molecular formula and its ¹H NMR spectrum:

b. C₆H₁₂O

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Identify each of the following compounds from the ¹H NMR data and molecular formula:

c. C₅H₁₀O₂: a 3H triplet at 1.15 ppm

a 3H triplet at 1.25 ppm

a 2H quartet at 2.33 ppm

a 2H quartet at 4.13 ppm

Describe the ¹H NMR spectrum you would expect for each of the following compounds, indicating the relative positions of the signals:

f.