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Chapter 17: Q51P (page 567)

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

. Propose a structure.

Short Answer

Expert verified

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

Step by step solution

01

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.

02

Structure of the alcohol with the formula C8H10O

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

The absorption at 2.43未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:

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Most popular questions from this chapter

How would you carry out the following transformations?

(a)

(b)

(c)

How would you prepare the following compounds from 1-phenylethanol?

More than one step may be required.

(a) Acetophenone

(b) Benzyl alcohol

(c) m-Bromobenzoic acid

(d) 2-Phenyl-2-propanol

p-Nitrophenol and 2,6-dimethyl-4-nitrophenol both have pKa 5 7.15, but 3,5-dimethyl-4-nitrophenol has pKa 5 8.25. Why is 3,5-dimethyl-4- nitrophenol so much less acidic?

Named bombykol, the sex pheromone secreted by the female silkworm

moth has the formula C16H28O and the systematic name (10E,12Z)-

10,12-hexadecadien-1-ol. Draw bombykol, showing the correct geometry

for the two double bonds.

What alcohols would give the following products on oxidation?

(a)

(b)

(c)
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