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Magazine Problem 65
For each of the following reagents, decide whether chlorobenzene will react with it or not, and, if it does, draw and name the products expected from the reaction. (a) \(\mathrm{Br}_{2}\) and \(\mathrm{FeBr}_{3}\) (b) \(\mathrm{HBr}\) (c) \(\mathrm{HNO}_{3}\) and \(\mathrm{H}_{2} \mathrm{SO}_{4}\) catalyst
Problem 68
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?
Problem 69
Salicylic acid (o-hydroxybenzoic acid) is used as starting material to prepare aspirin. Draw the structure of salicylic acid.
Problem 72
Assume that you have two unlabeled bottles, one with cyclohexane and one with cyclohexene. How could you tell them apart by carrying out chemical reactions?
Problem 75
Menthene, a compound found in mint plants, has the formula \(\mathrm{C}_{10} \mathrm{H}_{18}\) and the IUPAC name 1 -isopropyl4-methylcyclohexene. What is the structure of menthene?
Problem 78
Two products are possible when pent-2-ene is treated with HBr. Write the structures of the possible products, and explain why they are made in about equal amounts.
Problem 79
Ocimene, a compound isolated from the herb basil, has three double bonds and the IUPAC name 3,7 -dimethylocta1,3,6 -triene. (a) Draw its structure. (b) Draw the structure of the compound formed if enough HBr is added to react with all the double bonds in ocimene.
