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1 K E Y Please write the first three letters of your last name in the above boxes Organic Chemistry CH 310M/318M Dr. Sessler EXAM 1 Thursday, October 2, 2008 Name:_______________________________ UT EID:_____________________________ Signature:____________________________ NOTE: The exam must be taken using blue or black ink to be eligible for a regrade in the case you have concerns regarding grading errors.
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2 1. Name each of the following compounds according to acceptable IUPAC nomenclature guidelines. (24 points) I CH 2 H CH 3 H H H H H H 3 C disregard R-/S- stereochemistry 2,3-dimethyl-4-propylheptane 1-ethyl-2-methylcyclohexane ethylcyclopentane 3-ethyl-4-methylhexane Cl F Br 2-bromo-1-chloro-3-fluorobutane O butanone or 2-butanone 1-iodoheptane 3-isopropyl-2,4-dimethylpentane (3-methylethyl)
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3 2. Draw the chemical structures of the following compounds. (18 points) cycloheptanol 5-iodo-2-methylhexane cis -1,2-diethylcyclobutane cyclopropylcyclopentane propionic acid cyclopentene HO I O OH CH 2 CH 3 CH 2 CH 3
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4 3. Draw the Lewis dot structures for the following molecules. Use lines for bonds and dots for lone pairs of electrons. (18 points) a. CH 3 CH 2 CH 3 b. NH 3 c. CH 3 OCH 3 d. C 2 H 4 e. CH 2 O f. CH 3 N 3 4. Determine the overall charge for each of the following molecules/ions and write it in the box as shown for part a. Then draw the Lewis line structures below. Use lines for bonds and dots for lone pairs of electrons. Also where appropriate indicate any formal charges ( and ) on the correct atoms. Assume complete octets can be obtained in at least one stable resonance structure. (24 points) Other plausible structures were accepted for Parts A, C, and D. a. CH 3 NO 2 b. CO 2 c. OCN d. NH 2 e. CH 3 O f. NH 3 CH 2 CO 2 0 C H H H C H H C H H H N C H H H O C H H H N N N C C H H H H C O H H C H H H N H H C H H H O C H N H C O O H H H 0 -1 -1 -1 0 C H H H N O O C O O C N O
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5 5. Resonance structures a. Draw the two resonance structures for nitromethane (CH 3 NO 2 ) question 4a in the boxes below.
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Exam1key - Circle the section in which you are enrolled...

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