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19. Reactions of Aromatics: EAS and Beyond

EAS:Retrosynthesis

19. Reactions of Aromatics: EAS and Beyond

EAS:Retrosynthesis

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Aromatic synthesis starting with benzene/benzene derivatives

Aromatic synthesis starting with benzene/benzene derivatives

Johnny Betancourt

Synthesize the target molecule

Synthesize the target molecule

Johnny Betancourt

Synthesize the target molecule

Synthesize the target molecule

Johnny Betancourt

Practice this topic

Provide the reaction for each of the following reaction steps

Beginning from Benzene, synthesize the following compound.

Beginning from Benzene, synthesize the following compound.

1-Phenylethanol

Beginning from Benzene, synthesize the following compound.

Multiple Choice

Which synthesis will successfully form the given target with benzene as the starting material?

Textbook Question

The most common selective herbicide for killing broadleaf weeds is 2,4-dichlorophenoxyacetic acid (2,4-D). Show how you would synthesize 2,4-D from benzene, chloroacetic acid (ClCH2COOH), and any necessary reagents and solvents.

Textbook Question

Show how you would synthesize the following aromatic derivatives from benzene. (c) p-chlorotoluene

Textbook Question

Show how you would synthesize the following aromatic derivatives from benzene. (b) p-toluenesulfonic acid

Textbook Question

Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures. (b) 1-phenyl-1-methoxybutane

Textbook Question

Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures. (a) 1-phenyl-1-bromobutane

Textbook Question

Starting from toluene, propose a synthesis of this trisubstituted benzene.

Textbook Question

Propose a synthetic sequence of this trisubstituted benzene starting from toluene.

Textbook Question

Show how you would synthesize the following aromatic derivatives from benzene. (a) p-tert-butylnitrobenzene

Textbook Question

c. Acetaminophen is the active ingredient in Tylenol. How can acetominophen be synthesized from benzene?

Textbook Question

Show how the following compounds can be prepared from benzene: c.

Textbook Question

Describe how 3-methyl-1-phenyl-3-pentanol can be prepared from benzene. You can use any inorganic reagents and solvents, and any organic reagents provided they contain no more than two carbons.

Textbook Question

Benzene underwent a Friedel–Crafts acylation followed by a Wolff–Kishner reduction. The product gave the following 1H NMR spectrum. What acyl chloride was used in the Friedel–Crafts acylation?

Textbook Question

Beginning with benzene, synthesize the benzyl bromide shown. [You will use reactions from Chapters 23 and 24 in this synthesis.]

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Textbook Question

Beginning with benzene, synthesize the following substituted benzenes. The ideal number of steps is indicated.

(d) <IMAGE>

FROM THE LITERATURE The following steps were used in the synthesis of the antimalarial thiaplakortone A. Identify the missing reagents, (a) and (b),

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Textbook Question

Provide the necessary reagents next to the arrows.

Textbook Question

Phenolphthalein, a common nonprescription laxative, is also an acid–base indicator that is colorless in acid and red in base. Phenolphthalein is synthesized by the acid-catalyzed reaction of phthalic anhydride with 2 equivalents of phenol.

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(b) Propose a mechanism for the conversion of phenolphthalein to its red dianion in base.

(c) Use resonance structures to show that the two phenolic oxygen atoms are equivalent (each with half a negative charge) in the red phenolphthalein dianion.

Textbook Question

Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and>or Gatterman–Koch synthesis to prepare the following compounds:

(g) n-butylbenzene

Textbook Question

Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and>or Gatterman–Koch synthesis to prepare the following compounds:

(h) <IMAGE> (from benzene)

Textbook Question

Describe two synthetic routes for the preparation of p-methoxyaniline from benzene.

Textbook Question

Show how you would synthesize the following compounds, using the indicated starting materials. (a) 3-phenylbutan-1-ol from styrene

Textbook Question

The antioxidants BHA and BHT are commonly used as food preservatives. Show how BHA and BHT can be made from phenol and hydroquinone

Textbook Question

Predict the major product at the end of each sequence. (a)

Textbook Question

Predict the major product at the end of each sequence. (b)

Textbook Question

Starting with benzene and any other reagents you need, show how you would synthesize the compound shown here. (Hint: Consider a Pd-catalyzed coupling for the final step.)

Textbook Question

What products would you expect from the following coupling reactions? (c)

Textbook Question

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents. (b) <

Textbook Question

The following steps were used in the synthesis of the antimalarial thiaplakortone A. Identify the missing reagents, (a) and (b),

<IMAGE>

Textbook Question

Predict the product(s) of each of the following multistep reactions.

(a) <IMAGE>

Textbook Question

a. Describe three ways the following reaction can be carried out:

Textbook Question

b. Describe two ways the following reaction can be carried out:

Textbook Question

Show how you would accomplish the following syntheses. (a) benzene → n-butylbenzene

Textbook Question

Show how each of the following compounds can be synthesized from benzene: f. m-xylene

Textbook Question

Show how each of the following compounds can be synthesized from benzene: i. 1-phenyl-2-propanol

Textbook Question

Show how each of the following compounds can be synthesized from benzene: d. anisole

Textbook Question

Show how the following compounds can be synthesized from benzene: b. m-chloroethylbenzene

Textbook Question

Show how the following compounds can be synthesized from benzene: f. m-hydroxybenzoic acid

Textbook Question

Describe two ways to prepare anisole from benzene.

Textbook Question

Show how the following compounds can be synthesized from benzene: a. N,N,N-trimethylanilinium iodide

Textbook Question

How can you prepare the following compounds with benzene as one of the starting materials? c.

Textbook Question

How can you prepare the following compounds with benzene as one of the starting materials? d.

Textbook Question

Show how the following compounds can be synthesized from benzene: b.

Textbook Question

Show how each of the following compounds can be synthesized from benzene:

a. o-bromopropylbenzene

Textbook Question

Describe how naphthalene can be prepared from the given starting material.

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Textbook Question

Show how the following compounds can be synthesized from benzene:

a. <IMAGE>

Textbook Question

Show how each of the following compounds can be synthesized from benzene:

d. p-chloroaniline

Textbook Question

Show how each of the following compounds can be synthesized from benzene:

h. m-bromopropylbenzene

Textbook Question

Show how the following compounds can be synthesized from benzene:

d. m-methylnitrobenzene

Textbook Question

Show how the following compounds can be synthesized from benzene:

g. p-dideuteriobenzene

Textbook Question

Show how the following compounds can be synthesized from benzene:

h. p-nitro-N-methylaniline

Textbook Question

Show how each of the following compounds can be synthesized from benzene:

c. p-bromoanisole

Textbook Question

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

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a. How can tyramine be prepared from b-phenylethylamine?

Textbook Question

b. Ibuprofen is the active ingredient in pain relievers such as Advil, Motrin, and Nuprin. How can ibuprofen be synthesized from benzene?

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