Chem 2124 Essay

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CHEM 2124 Unit 2 Worksheet 2 1) Why does benzene undergo a substitution reaction with Br2 while cyclohexene undergoes an addition reaction? Addition of bromine to benzene is highly unfavorable because it would result in a non-aromatic product. 2) Which is more stable, cyclobutadiene or 1,3-butadiene? Explain 1,3-butadiene is more stable. Cyclobutadiene is antiaromatic and antiaromatic systems are less stable than their open chain counterparts. 3) Is the [10]annulene shown below aromatic? Explain. [pic] This is non-aromatic because it is a non-planar system. 4) Classify cyclopentadienyl cation as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network. The cyclopentadienyl cation is anti-aromatic with 4n pi electrons. 5) Provide the structure of the major organic product which results when phenanthrene is treated with Br2 in carbon tetrachloride. [pic] 6) Provide an acceptable name for the compound below. [pic] aniline, aminobenzene, benzenamine 7) Provide an acceptable name for the compound below. [pic]p-dichlorobenzene, 1,4-dichlorobenzene 8) Provide the structure of m-nitrophenol. [pic] 9) Provide the structure of indole. [pic] 10) The IR spectrum of m-xylene contains stretches which are characteristic of most aromatic hydrocarbons. List the peaks (in cm-1) associated with the aromatic C=C stretch and the aromatic C–H stretch. C-H just above 3000 cm-1, C=C ~ 1600 cm-1 11) How many distinct trichlorobenzene isomers are possible? 3 draw them! 12) When cyclohexene is treated with KMnO4, H2O, the syn-1,2-diol is produced. What reaction occurs when benzene is similarly treated? No Reaction 13) Nitrogen's lone pair electrons occupy what type of orbital in pyridine? A) s B) sp C) sp2 The answer is C D) sp3 E) p 14) Provide the structure of p-aminobenzoic acid. [pic] 15)

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