Question

The following ¹HNMR spectrum is that of an alcohol, C₈H₁₀O

. Propose a structure.

Short answer

The alcohol with the formula C₈H₁₀Othat satisfies the ¹H NMR data is 4-methylbenzylalcohol.

Step-by-step solution

1H NMR spectrum

Alcohols exhibit characteristic absorption in the ¹H NMR spectrum. Hydrogens on the oxygen bearing carbon atom are deshielded by the electron withdrawing effect of oxygen situated near to it.

Structure of the alcohol with the formula C8H10O

The symmetric doublets at 7.10$\delta$ and 7.17$\delta$ with a relative area of 3.00 indicate that the compound is a para substituted benzene derivative. The signal at 2.32$\delta$ with a relative area of 3.00 indicates that the methyl group is a para substituent. The absorption at 4.50$\delta$with a relative area of 2.00 indicates a carbon with two hydrogens connected to a hetero atom.

The absorption at 2.43$\delta$has a relative area of 1.00 is due to the alcoholic proton. Hence, the compound is p-methylbenzyl alcohol. The structure with the absorption values can be given as: