Organic Chemistry
Phenacetin is a medicine used to treat mild to moderate pain. Complete the following synthetic scheme used to synthesize phenacetin:
Note: Hints are provided as needed.
Propose a synthetic scheme to produce the indicated C−O bond of the given compound. (Note: –CCl3, which is an electron-withdrawing group, is para to the position where the new bond will form.)
Propose a synthesis for the following compound using benzene as the starting material.
Identify the required reagents for the given reaction sequence.
The compound below is involved in the synthesis of proxymetacaine. Show how to synthesize the compound from phenol.
Benzene undergoes Friedel-Crafts alkylation with an unknown alkyl chloride. The 1H NMR spectrum of the product is shown below. Identify the alkyl chloride used.
Provide the correct reaction sequence for the synthesis of the the aromatic derivative m-nitroacetophenone starting from benzene.
Write the correct synthetic sequence for preparation of the following compound using Friedel–Crafts acylation and/or Clemmensen reduction.
Write the correct synthetic sequence for the conversion of ethylbenzene to the given trisubstituted benzene.
Provide the correct synthetic sequence for the conversion of ethylbenzene to the given trisubstituted benzene.
Propose the synthesis of the given compound starting from toluene. Consider that the para product is the major product and is separable from other products:
1-(bromomethyl)-4-propylbenzene
1-(ethoxymethyl)-4-propylbenzene
Provide the correct reaction sequence for the synthesis of the aromatic derivative p-isopropylbenzenesulfonic acid starting from benzene.
Provide the correct reaction sequence for the synthesis of the aromatic derivative m-bromoacetophenone starting from benzene.
2-methyl-4-chlorophenoxyacetic acid (MCPA) is a herbicide widely used for killing broadleaf weeds. Write the correct reaction sequence for the synthesis of MCPA, starting with phenol and other required reagents and solvents.
Starting with benzene, how is 1-bromo-3-(1-bromobutyl)benzene synthesized?
With benzene as the starting material, provide the synthetic scheme for the substituted benzene shown below using the number of ideal steps indicated.
