13. Alkenes, Alkynes, and Aromatic Compounds

Name the product of the following benzene halogenation reaction.

Provide a complete reaction of benzene Friedel Crafts alkylation with 2-bromo-2-methylpropane and name the product.

Fill in the missing reagent for the provided reaction.

Reaction of Br₂ and FeBr₃ with phenol can lead to three possible substitution products. Show the structure of each and name them.

Aromatic compounds do not normally react with hydrogen in the presence of a palladium catalyst but will if very high pressures (200 atm) and high temperatures are used. Under these conditions, toluene adds three molecules of H₂ to give an alkane addition product. What is a likely structure for the product?

The explosive trinitrotoluene (TNT) is made by carrying out three successive nitration reactions on toluene. If these nitrations only occur in the ortho and para positions relative to the methyl group, what is the structure of TNT?

Phenols undergo the same kind of substitution reactions that other aromatic compounds do (Section 13.11). Formulate the reaction of p-methylphenol with Br₂ to give a mixture of two substitution products.

Ocimene, a compound isolated from the herb basil, has three double bonds and the IUPAC name 3,7-dimethyl-1, 3-6-octatriene.

b. Draw the structure of the compound formed if enough HBr is added to react with all the double bonds in ocimene.

Cinnamaldehyde, the pleasant-smelling substance found in cinnamon oil, has the following structure:

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What products would you expect to obtain from reaction of cinnamaldehyde with water and sulfuric acid catalyst?