Spring 2010 Exam 1 - Name ‘ CHEM 2323 Organic Chemistry I...

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Unformatted text preview: Name: ‘ CHEM 2323 Organic Chemistry I i 1 . Instructor: Dr. Shawn Amorde ._ Test 1A fl . Spring 2010 i u Scratch paper ‘ 1/2 page with written notes ‘ 1' , General Instructions: {I All answers need to be in ink if you request a re-grade. Work on all problems must be shown W - for full credit. Label drawings clearly and circle final answers where applicable. All problems are 10 pts unless noted. k 1. Please name the following alkane. a. Label all primary, secondary, and tertiary carbons. H30 ‘\ l ‘5’ b. Please give the best Newman projection looking down C4-C5 2. Octane, Cngg has 18 different constitutional isomers. (20 pts) a. Please draw at least 4 different isomers, each containing a different length parent chain. (heptane, hexane, pentane, and butane) b. Provide the names for each isomer under each structure. c. Please label all primary (1°), secondary (2°), tertiary (3°), and quaternary carbons (4°). ‘J‘y‘.vl ' t ' I’ ;ya~ 1’ x Now, label the carbons on the isomer containing the hexane parent chain with the numbers 1-6. Looking down the C3-C4 bond, draw Newman projections for the anti and the gauche conformations. Which is lower in overall molecular energy? 3. Please draw the skeletal structure for 1,2—diisopropylcyclohexane.(10 pt) a. Please draw two possible conformational isomers of this compound. b. Please draw two configurational isomers of this compound. c. Please give the best chair for this compound. 4. Please give the flat (pancake) skeletal structure (with bolds and dashes) for the following chairs as drawn; H30 l“-~\ i V H F l l\ If) 5. Please give the best chair for the following compounds as drawn; Hgo CH3 l H c , ' H3C 3 i KN“) ,. {I /l “‘3 X XX CH3 Pt CH3 I! H300, “\\\\ ‘ ’ I! \\\\ )\ i /\ L 6. Please identify whether the following compounds (from question 7) are constitutional isomers, configurational isomers, conformational isomers, or the same compounds. CH3 H30“ 7. Please draw the following cyclohexanes in the chair conformation, including the egair and the chair flip. trans—1,2—dimethyl cyclohexane H30“ Please give the skeletal structure for the following compounds. 21. cyclopentylcyclohexane b. 4-cyclopropyl-3—n1ethyloctane c. cis-l-ethyl-2-methylcyclobutane l“~l,.._<./,’./ < 9. Road Map Problem; Given the following set of guidelines, can you draw an isomer which fits the following set of guidelines? Draw as many as you can, show all your structures for partial credit; use scratch paper if needed and turn in with the test. The molecular formula is C10H20. No alkenes present No cyclobutane The structure contains; 4 primary carbons 2 secondary carbons 4 tertiary carbons e. Plane of symmetry P‘PP‘?’ Bonus!! Given the following set of guidelines, can you draw an isomer which fits the following set of guidelines? a. The molecular formula is CIOHZO. b. The structure contains at least; 2 primary carbons 2 secondary carbons 2 tertiary carbon c. Contains a plane of symmetry and is C2 symmetric ...
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Spring 2010 Exam 1 - Name ‘ CHEM 2323 Organic Chemistry I...

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