PracticeCh16Ques - Organic Chemistry 7e(Wade Chapter 16...

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1 Organic Chemistry, 7e (Wade) Chapter 16 Aromatic Compounds 1) Which of the following is an incorrect description of benzene? A) The CCC bond angles are all equal to 120°. B) The molecule is planar. C) The molecule is a 6-membered ring which contains alternating single and double carbon- carbon bonds. D) The molecule is aromatic. E) The molecule can be drawn as a resonance hybrid of two Kekule structures. 2) What is the bond order of the carbon-carbon bonds in benzene? 3) Cyclic hydrocarbons which can be represented as structures containing alternating single and double bonds are called __________. 4) When cyclohexene is treated with KMnO 4 , H 2 O, the syn -1,2-diol is produced. What reaction occurs when benzene is similarly treated? 5) Why does benzene undergo a substitution reaction with Br 2 while cyclohexene undergoes an addition reaction. 6) What is suggested by the fact that benzene's molar heat of hydrogenation is 36 kcal less than three times the molar heat of hydrogenation of cyclohexene? 7) In the molecular orbital representation of benzene, how many π molecular orbitals are present? 8) How many distinct nodal planes which are perpendicular to the molecular plane are present in the π 4 * orbital of benzene? 9) How many pairs of degenerate π molecular orbitals are found in benzene? A) 6
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2 B) 5 C) 4 D) 3 E) 2 10) Which of the following undergoes S N 2 reaction with sodium methoxide most rapidly? 11) Which of the following undergoes solvolysis in methanol most rapidly? 12) Provide a diagram which depicts the relative energies of the π molecular orbitals of benz ene. Show which molecular orbitals are filled in benzene's ground state. 13) Show how the participating p orbitals interact to form the highest energy π molecular orbital of benzene. 14) Show how the p orbitals overlap to generate the p 4 * of cyclobutadiene. 15) Describe the occupied p molecular orbitals in the ground state of cyclobutadiene. 16) What is the major difference between an antiaromatic and aromatic compound? A) The structure must be cyclic for aromatic but not antiaromatic compounds? B) Antiaromatic compounds have at least one sp 3 hybridized atom in the ring C) Antiaromatic compounds can assume a chair-like structure while aromatic compounds are nearly flat D) Aromatic compounds cannot have a charged atom in the structure E) Only aromatic compounds follow Huckel ’s rule.
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