What is the expected multiplicity of the signal of the circled hydrogen atoms in a 1H NMR spectrum?

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Begin by identifying how the multiplicity in 1H NMR arises: a proton’s signal is split by neighboring nonequivalent protons, and the splitting follows the n+1 rule, where n is the number of neighboring hydrogens.

Option a: doublet. This would occur if the circled hydrogen were coupled to exactly one neighboring hydrogen. If there were two or more neighbors, the splitting would be more complex than a simple doublet, so thisSingle-neighbor scenario is likely incorrect here.

Option b: singlet. A singlet means there are no neighboring hydrogens that can couple with the circled proton, or all couplings cancel out. If the circled hydrogen is adjacent to any hydrogen-bearing carbon, some coupling would typically appear, making a singlet unlikely unless the neighboring substituents decouple or are magnetically equivalent with no coupling, which is unusual in a standard hydrocarbon context.

Option c: triplet. According to the n+1 rule, if the circled hydrogen has two neighboring hydrogens on an adjacent carbon (i.e., it is split by two equivalent protons), the signal will appear as a triplet (3 lines). This is a common pattern for a CH group flanked by two equivalent H on the next carbon, or a CH2 group adjacent to a CH2 or CH3 where the coupling to those two equivalent protons produces three peaks.

Option d: quartet. A quartet would arise if the circled proton were coupled to three neighboring hydrogens. If there were three equivalent protons attached to the neighboring carbon, the splitting would yield four lines. This would require the circled hydrogen to be near a CH3 group as the coupling partner, which is not implied by the circled position alone.

Thus, the most consistent explanation—given the circled hydrogen’s coupling to two equivalent neighboring hydrogens—is that the signal should be a triplet. The other options describe splittings that would require different neighboring proton counts or arrangements, which do not align with the typical two-neighbor scenario.

MUF0042 Chemistry Unit 2 - Semester 2, 2025 8.20 Quiz: NMR Spectroscopy

What is the expected multiplicity of the signal of the circled hydrogen atoms in a 1H NMR spectrum?

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