3351 midterm 1 - Chemistry 3351-100 Organic Chemistry Dr...

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Unformatted text preview: Chemistry 3351-100 Organic Chemistry/ Dr. Barney Ellison Thursday: Sept. 27th @ 7:00pm —3 9:00 / 1St Exam/_He11ems 252 Name: kgE (please print) 1. (10 pts) For each of the following resonance hybrids, rank the contributing structures in order of their relative importance: :o: :5: — H “‘—” | /C\-- /C\ a) H CH2“ H \CH2 M MD“- :o: :3: — II +—’“ I /C\-- /C + b) H NH2 H \NH2 Wm”. M c) :o: :8: — :O' + + T. | HECZC—CH i—h HQC—C=CH 4—————- H20—0=CH H H H \MosJr 0k emit 2. (20 pts) Arrange the following compounds in order of increasing CO bond length. £11)CHE,,OCH3 b) CH3COCH3 c)CH3co; d)CO 67 (9 ® 0 ® 5) c’ :'—- :C‘ so {O‘Ncu CH5 "C “CR5 Gug- \‘b UM; 5 gkwws 95x35 Arrange the following compounds in order of increasing C-N bond length. a) CHSCN b) (CH3)2C=NOH c) 1—1 y + d) (:ngle2 '3 ® 3. 2. O “s ,0“ 1. GD CEN 1F” -C:—, H EN cm] W A TN \ all) l; \J A:: NH ‘~ 9“ RCMP: 7 ‘5 ‘5." N 7 3. (10 pts) Write out Kekule structures for the following species. Be sure to indicate lone pairs of electrons. I. 0.. Here is the Kekulé for water: H/ \H a) CENO ‘N: P. n / HQ}. b) CHZCCHZ —- :2. C,“ M2;— C L c) 02— «- ‘1': v ' [es s“? 9““? d) CHBCHNH rfi Us 5 7.:— Nut 4. (10 pts) Explain the acidity orders. a) H2504 > HSO — \ QM... O 4 o + 50150“ . ‘6; SAW 1 H AA- 0 O \‘4 0 3 __ cloa- “ “W9 Ao‘éo- "*7 W” 30% C \& ‘o b) nitric acid (HONOZ) > nitrous acid (HONO) \ i V w k *— (I 0 I?" \A a— O-«N o 1—\o'— {C QM“ A‘M‘Q 0W 3 3X38“; c) nitrous acid (HONO) > hydroxylamine (NHZOH) \ J, c a PM W": 4' *DwN “ml-O + \‘D (W { 0x681,“ 2 Mag-«.3 d) H25 > PH3 S 4; MM MMAZM m P 5. (10 pts) Using Newman projections, draw a potential energy diagram for rotation about the Cz—C3 bond of 2,3—dimethy1butane. 6. (10 pts) Using simpie geometric figures and line structures, depict the following compounds. a) 1, 1, 3~trimethylcyclohexane “"3 (\fcfi; [:::k cHg b) 3-cyclopenty1pentane fl ,fl :><\ g2 c) 1-chl0r0-4-ch10r0methy1cyclohexane CR A) ~HN£M§£ d) 1, 1, 2, 2,—tetramethylcyclopropane 7. (10 pts) Which of the following pairs are structural isomers? Conformational isomers? Neither ? CH3 H30 Or ‘3‘ M}: a) CH3 or H H30 CH3 H30 CH3 Q ‘5. £1»! "Q {wa H or 02 CE b) H H H 52 H H H3C H $4 " “* AM CHSCHz CH2CH3 CHgoH2 CHECH3 CH3 8. (10 pts) Draw a Newman projection for the Cl—C2 bond of methylcyclohexane with the methyl group in the equatorial position. Compare this with the ring flipped so the methyl group is in the axial position. Which conformation is more stable? Why? C 3 C.\\ it JP ix 4 l W n l3 )\ x l A C H / Gig Pr/ \GN” 3: l I \‘c CA!» is; 6:33 W AFC”) -10- 9. (10 pts) The reaction of the unusual hydrocarbon, spiropentane with chlorine and light is a nice method to prepare chlorospiropentane. H H C OH or H o C/C’f 2l\C/| 2 2 2]\C/ H20/ \CH2 11" H20/ \CH2 Z a) Why is this reaction so useful? b) Draw me the reaction mechanism. Assume that you have a large excess of spiropentane. ...
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