6:19 PM 58 1. Write the structural formula for each of the following: (a) m-xylene (b) 3,5-dinitrobenzoic acid (c) 2,4,6-trinitrophenol (d) Chlorotriphenylmethane (e) p-ethylaniline (f) 4-n-butylbenzenesulfonic acid (g) 1-chloro-2-(2-chloropropyl)benzene (h) \( m \)-bromo-anisole (i) Benzyl alcohol (j) 4-Phenyl-1-butene (k) \( o \) - \( p \) Cresol (l) 2-Phenylethanol 2. Which of the following molecules would you expect to be aromatic, anti-aromatic or non-aromatic? (i) (ii) (iii) (v) (vi) (vii) (viii) (ix) (x) (xi) (xiii) (xiii) 3. Which of the hydrogen atoms shown below is more acidic? Explain your answer. A B 4. Starting with benzene outline the synthesis of each of the following compounds: (a) \( m \)-bromonitrobenzene (b) Ortho-chloronitrobenzene (c) p-chlorobenzenesulfonic acid (d) p-nitrobenzoic acid (e) \( m \)-toluidine (f) n-butylbenzene ONLY 5. Provide a detailed mechanism for each of the following reactions. Include contributing resonance structures and resonance hybrid for the arenium ion intermediate. (i) (ii) (iii) 6. Predict the major product (or products) formed when each of the following reacts with \( \mathrm{Cl}_{2} \) and \( \mathrm{FeCl}_{3} \) : (a) Tert-butyl benzene (e) Acetanilide (b) Phenol (f) Benzonitrile (c) Iodobenzene (g) Naphthalene (d) Aniline (h) Trifluoromethylbenzene 7. Predict the major product (or products) formed when each of the following reacts with \( \mathrm{HNO}_{3} \) and \( \mathrm{H}_{2} \mathrm{SO}_{4} \). (a) Phenyl benzoate (b) Anisole (c) Toluene 8. Write a mechanism to account for the products of the following reactions: (i) (ii) 2
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Structural formulas: (a) m-xylene:  (b) 3,5-dinitrobenzoic acid: ![3,5-dinitrobenzoic Show more…
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8.52 Deduce the structures of compounds $\mathbf{A}, \mathbf{B},$ and $\mathbf{C},$ which all have the formula $\mathrm{C}_{6} \mathrm{H}_{10} .$ As you read the information that follows, draw reaction flowcharts (roadmaps) like those in Problems 8.24 and $8.49 .$ This approach will help you solve the problem. All three compounds rapidly decolorize bromine; all three are soluble in cold concentrated sulfuric acid. Compound A has an absorption in its IR spectrum at about $3300 \mathrm{cm}^{-1}$, but compounds $\mathrm{B}$ and $\mathrm{C}$ do not. Compounds $\mathrm{A}$ and $\mathrm{B}$ both yield hexane when they are treated with excess hydrogen in the presence of a platinum catalyst. Under these conditions Cabsorbs only one molar equivalent of hydrogen and gives a product with the formula $\mathrm{C}_{6} \mathrm{H}_{12} .$ When $\mathrm{A}$ is oxidized with hot basic $\mathrm{KMnO}_{4}$ and the resulting solution acidified,the only organic product that can be isolated is(FIGURE CAN'T COPY) Similar oxidation of B gives only (FIGURE CAN'T COPY) and similar treatment of $\mathbf{C}$ gives only $\mathrm{HO}$ (FIGURE CAN'T COPY)
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