BackShow 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
Ibuprofen is the active ingredient in pain relievers such as Advil, Motrin, and Nuprin. How can ibuprofen be synthesized from benzene?
Show how the following compounds can be synthesized from benzene:
g. p-dideuteriobenzene
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?
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Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.
d. How can b-phenylethylamine be prepared from benzyl chloride?
Show how you would synthesize the following compounds, using the indicated starting materials.
(a) 3-phenylbutan-1-ol from styrene
Provide the necessary reagents next to the arrows.
Describe how naphthalene can be prepared from the given starting material.
Beginning from Benzene, synthesize the following compound.
1-Phenylethanol
Show how each of the following compounds can be synthesized from benzene:
h. m-bromopropylbenzene
Describe two synthetic routes for the preparation of p-methoxyaniline from benzene.
Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and/or Gatterman–Koch synthesis to prepare the following compounds:
h.
Suggest a synthesis of each of the molecules shown beginning with benzene.
(c)
a. Describe three ways the following reaction can be carried out:
Pyrrole undergoes electrophilic aromatic substitution more readily than benzene, and mild reagents and conditions are sufficient. These reactions normally occur at the 2-position rather than the 3-position, as shown in the following example.
a. Propose a mechanism for the acetylation of pyrrole just shown. You may begin with pyrrole and the acylium ion, CH3C≡O+. Be careful to draw all the resonance structures of the intermediate.