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Chapter 18: Q97P (page 921)

An unknown compound reacts with ethyl chloride and aluminum trichloride to form a compound that has the following 1H NMR spectrum. What is thestructure of the compound?

Short Answer

Expert verified

Proton NMR finds the organic molecule's structure byconsidering the proton environmentof the compound.

The number of peaks/signals in the proton NMR spectrum (graph plot between ppm value and energy absorbed) tells the number of different proton environments present in the compound.

Step by step solution

01

Proton NMR

Proton NMR finds the organic molecule's structure byconsidering the proton environmentof the compound.

The number of peaks/signals in the proton NMR spectrum (graph plot between ppm value and energy absorbed) tells the number of different proton environments present in the compound.

02

Structure of compound

An unknown compound reacts with ethyl chloride and aluminum trichloride to form a compound with the 1H NMR spectrum having the unsplit signal at 7.1 that is of benzene hydrogen in the product is chemically equivalent. The triplet at 1.2 ppm of -CH2 hydrogen and quartet at 2.6 ppm is -CH3the hydrogen of the ethyl group.

Thus the compound form in the product is 1,4-diethylbenzene, and the unknown compound from which it is formed is ethylbenzene, shown as follows:

Formation of1,4-diethylbenzene

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Most popular questions from this chapter

Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.

Tyramine Dopamine

a. How can tyramine be prepared from \({\bf{\beta }}\)-phenylethylamine?

b. How can dopamine be prepared from tyramine?

c. Give two ways to prepare \({\bf{\beta }}\) -phenylethylamine from \({\bf{\beta }}\)-phenylethyl chloride.

d. How can \({\bf{\beta }}\)-phenylethylamine be prepared from benzyl chloride?

e. How can \({\bf{\beta }}\)- phenylethylamine be prepared from benzaldehyde?

Does m-xylene or p-xylene react more rapidly with Cl2 + FeCl3? Explain your answer.

Write the sequence of steps required for the conversion of benzene into benzenediazonium chloride.

Question: What reagents are required to carry out the following synthesis?

Benzene underwent a Friedel鈥揅rafts acylation followed by a Wolff鈥揔ishner reduction. The product gave the following 1H NMR spectrum. What acylchloride was used in the Friedel鈥揅rafts acylation?
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