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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
(d) ethoxybenzene
(g) p-aminobenzoic acid
(j) 3-nitro-4-bromobenzoic acid
(m) 2-(4-methylphenyl)butan-2-ol
(b) 1-phenyl-1-methoxybutane
(c) 3-phenylpropan-1-ol
(e) 1,2-dichloro-4-nitrobenzene
(f) 1-phenylpropan-2-ol
(h) 2-methyl-1-phenylbutan-2-ol
(i) 5-chloro-2-methylaniline
(k) 3-nitro-5-bromobenzoic acid
(l) 4-butylphenol

1 Answer

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Final answer:

To synthesize 3-phenylpropan-1-ol using benzene or toluene, start with benzene and use acetic acid and sodium permanganate as reagents. To synthesize 3-nitro-5-bromobenzoic acid, start with toluene and use nitric acid and bromine as reagents. To synthesize 4-butylphenol, start with benzene and use butyl bromide and a strong base.

Step-by-step explanation:

To synthesize 3-phenylpropan-1-ol using benzene or toluene, we can start with benzene and use acetic acid and sodium permanganate as reagents. The first step is to convert benzene to acetophenone using a Friedel-Crafts acylation reaction. Acetophenone is then reduced to 1-phenyl-2-propanol using sodium borohydride. Finally, the compound is further reduced to 3-phenylpropan-1-ol using hydrogenation.

To synthesize 3-nitro-5-bromobenzoic acid, we can start with toluene and use nitric acid and bromine as reagents. The first step is to substitute one hydrogen atom on toluene with a bromine atom using free radical bromination. The resulting compound is then nitrated using a mixture of nitric acid and sulfuric acid. The nitro group is then reduced to an amine group using hydrogenation. Lastly, the amine group is oxidized to a carboxylic acid using potassium permanganate or sodium dichromate.

To synthesize 4-butylphenol, we can start with benzene and use butyl bromide and a strong base such as sodium hydroxide. The first step is to substitute one hydrogen atom on benzene with a butyl group using an electrophilic aromatic substitution reaction. The resulting compound is then oxidized to a phenol using a mixture of potassium dichromate and sulfuric acid. Finally, the butyl group is reduced to a hydroxyl group using hydrogenation.

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