2005 summer exam - NAME Soc Sec XXX—XX Introductory Organic Chemistry 030.205.01 MIDTERM EXAM#1 Problem Points 12/15/4/12 E I& p—A

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Unformatted text preview: NAME Soc Sec # XXX—XX- Introductory Organic Chemistry 030.205.01 MIDTERM EXAM #1 June 17, 2005 Problem # Points / 12 /15 /4 /12 E I!& p—A p—a )—-A O \ /12 /4 p—l N )—l A b p—b LA) \ r—d r—I H \1 O\ U! !!h TOTAL / 100 1) For each labeled carbon atom in the molecule below, identify the hybridization state and the geometry: (1 pt each) 5/ O hybridization state hybridization state a) d) geometry geometry hybridization state hybridization state b) e) geometry geometry hybridization state f hybridization state C) geometry ) geometry 2) Name the following compounds: (5 pts each) /l\v>(; NAME I NAME \\ OH CI OH \I::]’ NAME l” Me 3) Identify any formal charges in each of the following cases: (1 pt each) '6' . :o’H a) {5N9} b) c) AO/ d) /\/N\/\ 4) Draw resonance structures for the following compounds (show the curved arrows): (2 pts each) 5) Consider the compound below: Et l" Me a) Draw both chair conformations of this compound, and circle the conformation that is more stable. (5 pts) 6) Using a Newman Projection, draw the most stable conformation of 1,2-dichloroethane: (2 pts) ‘ 7) Show the mechanism (curved arrows) for the following acid—base reaction: (2 pts) 8) Place a circle around each of the stereocenters in the following molecule. Then assign the configuration of each stereocenter (label each one as either R or S): (8 pts) 9) Draw the enantiomer of the following compound: (2 pts) 9H 9H Cl Cl OH 0 W Me Me ANSWER 10) For each pair of compounds below, circle the compound that is more acidic: (2 pts each) OH SH p C OH OH hi: 6 OH OH Cl Cl Cl Cl 0) Cl 11) For each of the following pairs of compounds, determine Whether the compounds are structural isomers, or enantiomers, or diastereomers, or the same compound: (2 pts each) 0 H o H HO H HO H H OH HO H CHZOH CHZOH Relationship (70' Cl ""cn Relationship - I I l | O Relationship E: H H H me J\/\ Me Relationship w CC Relationship \‘\\ Relationship 12) Circle the compounds that are optically active (4 pts): 0 .\\\Cl H E (1 H0 H “323:” A Cl H OH H Me Me CHZOH 13) The following Newman Projection represents a compound that is NOT in its most stable conformation: Et Me Et H H H Using Newman Projections, draw the most stable conformation and the least stable conformation for this compound. (2 pts each) MOST STABLE LEAST STABLE 14) How many different stereoisorners can be drawn for 1,2—dirnethylcyclohexane. Circle your answer: (2 pts) a)l b)2 c)3 d)4 e)6 15) Consider the following chair conformation below, and draw the ring flip: (2 pts) OH mm ANSWER l6) Predict the position of the equilibrium for the following reaction (if you think the equilibrium leans to the left, then circle the left side; if you think it leans to the right, then circle the right side) - 2 pts 0 e O 17) In class, we looked at energy diagrams that showed conformational analysis (we saw ethane, propane, and butane). Based on what we learned, draw an energy diagram that shows a conformational analysis of 1,2-dichloroethane. You do NOT need to draw all six Newman Projections in order to receive full credit. Simply draw the shape of the energy diagram. BUT, make sure to clearly label (identify) the parts of the diagram that correspond to the following: (4 pts) a) the most stable conformation b) the least stable conformation c) the conformations with gauche interactions ...
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This test prep was uploaded on 04/15/2008 for the course CHEMISTRY 030.205 taught by Professor Greenberg during the Fall '08 term at Johns Hopkins.

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2005 summer exam - NAME Soc Sec XXX—XX Introductory Organic Chemistry 030.205.01 MIDTERM EXAM#1 Problem Points 12/15/4/12 E I& p—A

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