CH310-Exam3 - UTID: _ VERSION A 11/17/2008 CH310N-Exam III...

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UTID: ________________________ VERSION A 11/17/2008 1 CH310N-Exam III Objective Test Section Identify the choice that best completes the statement or answers the question. There is only one correct answer; please carefully bubble your choice on the scantron sheet. (3pts. ea; 75 pts this section) 1. Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions? a. Cl, CN, NO 2 b. Cl, NH 2 , CH 3 c. CH 3 , OCH 3 , COCH 3 d. CH 3 , NH 2 , OCH 3 2. Which of the following compounds is antiaromatic? a. ethane b. cyclobutadiene c. benzene d. cyclooctatetraene 3. What is the major organic product obtained from the following reaction? a. 1 b. 2 c. 3 d. 4 4. Which of the following is not one of Hückel's criteria for aromaticity? a. The compound must be cyclic b. The compound must have one p-orbital on each atom of a ring c. The compound must be planar or nearly planar so that there is a continuous overlap of p orbitals d. The compound must have a closed loop of six pi electrons
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2 5. What is the major organic product obtained from the following reaction? a. 1 b. 2 c. 3 d. 4 6. What are the relative positions of the substituents in the following structure? a. anti b. meta c. ortho d. para 7. What is the IUPAC name of the following compound? a. 2-nitro-6-carboxybromobenzene b. 2-bromo-1-nitro-4-benzoic acid c. 2-bromo-4-carboxynitrobenzene d. 3-bromo-4-nitrobenzoic acid
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3 8. What is the major organic product obtained from the following reaction? a. 1 b. 2 c. 3 d. 4 9. Which of the following has the compounds shown in the correct order of decreasing acidity (i.e., more acidic > less acidic)? a. 1 > 2 > 3 b. 2 > 3 > 1 c. 3 > 2 > 1 d. 1 > 3 > 2 10. Which of the following compounds are secondary (2 ° ) amines? 1. (CH 3 ) 3 CNHCH 3 2. CH 3 CH(NH 2 )CH 2 CH 3 3. CH 3 CH 2 CH 2 NHCH 3 4. CH 3 CH 2 CH 2 CH 2 CH 2 NH 2 a. 1 and 2 b. 1 and 3 c. 1 , 2 and 3 d. 1 , 2 , 3 and 4
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4 11. What is the major organic product obtained from the following reaction? a. 1 b. 2 c. 3 d. 4 12. What is the major organic product obtained from the following reaction? a. 1 b. 2 c. 3 d. 4 13. What is the best choice of reagent to achieve the following reaction? a. Br 2 , CCl 4 b. HBr, H 2 O c. Br 2 , light d. NaBr
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5 14. Which of the following sets of substituents are all meta directing in electrophilic aromatic substitution reactions? a. CN, NO 2, COCH 3 b. CH 3 , OCH 3 , COCH 3 c. Cl, NH 2 , CH 3 d. CH 3 , NH 3 , OCH 3 15. What is the major organic product obtained from the following reaction? a. 1 b. 2 c. 3 d. 4 16. Which of the following undergoes the most rapid bromination upon treatment with Br 2 /FeBr 3 ? a. benzene b. nitrobenzene c. bromobenzene d. anisole
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6 17. Which of the following reaction coordinate diagrams explains the formation of different thermodynamic (T) and kinetic products from the same reactants (R)? a.
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CH310-Exam3 - UTID: _ VERSION A 11/17/2008 CH310N-Exam III...

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