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Chapter 18: Q 105 P (page 923)

Question: Show how lidocain, one of the most widely used injectable anesthetics, can be prepared from benzene and compounds containing no more than four carbons.

lidocain

Short Answer

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Step by step solution

01

Benzene

The benzene can be used for the synthesis of organic compounds containing large substituents. The compounds like Novocain and lidocain can be synthesized from benzene using a series of chemical reactions using different reagents.

02

Explanation

The reaction for the synthesis of lidocain is as given below.

The Friedel- Crafts reaction can be done on a ring with a sulfonic acid group, because its deactivation is offset by the activating amide group. The sulfonic acid group is put on the ring to block the para position and thereby force the methyl groups to go to the ortho positions.

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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?

Show how the following compounds can be synthesized from benzene:

a. m-chlorobenzenesulfonic acid

b. m-chloroethylbenzene

c. m-chlorobenzonitrile

d. 1-phenylpentane

e. m-bromobenzoic acid

f. m-hydroxybenzoic acid

g. p-cresol

h. benzyl alcohol

i. benzylamine

Draw the product of each of the following reactions:

a.

b.

Show the mechanism for the generation of the acylium ion if an acid anhydride is used instead of an acyl chloride for the source of the acylium ion.

Show how the following compounds can be synthesized from benzene:

a. N,N,N-trimethylanilinium iodide

b. 2-methyl-4-nitrophenol

c. p-benzylchlorobenzene

d. benzyl methyl ether

e. p-nitroaniline

f. m-bromoiodobenzene

g. p-dideuteriobenzene

h. p-nitro-N-methylaniline

i. 1-bromo-3-nitrobenzene
See all solutions

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