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Practice Exam MQ1 - Aut 2010 Chem 237B MidQuarter sec(11 1...

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Unformatted text preview: Aut. 2010 Chem 237B MidQuarter ' sec (11) 1. Name the following compounds: a) H b) r , c) CHZOH ‘1. \ in ' CHBCHZ \‘2\CHZCH3 C H 3 -. H C “2 CL CL ' a) b) C) (10) 2. Provide rationalizations for the following experimental observations: trans-Z-butene and cis-Z-butene are stable and do not interconvert thermally; but, in the presence of a catalytic amount of a strong acid (e. g. HBr or H2804) an equilibrium mixture of the two stereoisomers is rapidly formed. ’ ' (04) 3. Draw a Newman projection of the gauche conformer of l-chloropropane. (10) 4. Rank the following compounds as to their relative basicity. Use the following scale: 1 = . strongest base, 5 = weakest base. Br H20 HZS [CHzCHO] _ CH3O _ rank Ant. 2010 Chem 237B MidQuarter p. 2 sec (11) 5. Draw four (4) constitutional isomers of C3H5Cl. (20) 6. Fill in the missing reagents, products or starting materials. Br (Y J: O” W“ _._.__.__4 ._.___._.——9 V CH30H oH \€\ 4—“ . “—9 O KOH + K4— H20 (04) 7. Show the electron flow 03y arrow pushing) for the rate determining step in the E2 - mechanism of dehydrobromination under basic conditions. Use B3 _ as the “base”. Aut. 2010 Chem 237B MidQuarter p. 3 I sec (15) 8. Draw Lewis structures for: a) CH3N02 and its conjugate base. b) CH2N2 and its conjugate acid. (09) 9. Show a plot of potential energy versus rotation about the C2—C3 bond of 2-methylbutane. You should show the energy as a function of the projected angle (plot it over the 0 — 180 Orange) between the bonds to H3C* and H* in the structure below. CH H3C* C/ 3 \ / \ * ,C \ H A H I CH3 ~ H e . if \f m * , c" H be sure +0 [A52] energy M175! 0 60 a [20 I800 / [- (05) 10. Which of the compounds below has the larger molecular dipole ? Provide your rationale. Cl—CHz—CO-CI or CH3-CO-CI Aut. 2010 Chem 237B MidQuarter p. 4 . sec (10) 11. Show the detailed mechanism for the reaction below. Yes, the product is correct !‘ CH3 Ye H2014 H2504 CH3\§H\CH3 05/ CH3 (10) 12. The two stereoisomers below have an unusually large difference in stability (ca. 5 kcal). Figure out which is more stable and so indicate. Explain Why the energy difference is so large. You ' will likely need to draw the favored chair conformation of each isomers. Me Me. Me Me “'53“ ‘0 +Bu. ...
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