234-PS2-FA08-ANS - Organic Chemistry 1 — Problem Set#2...

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Unformatted text preview: Organic Chemistry 1 — Problem Set #2 — Bonding Name: 1. Draw Lewis clot structures for the following molecules. A) Two isomers of C4H10 NA B) Three isomers of (271-112, including one with a ring, and one with a triple bond. WW + M Ma Q» .g r . C) Cis/trans isomers of (HOZC)CHCH(COZH) gafi‘g“ % a“ C»; 343'; i £43m r M\..W/M"W w WM. Li» 3% g; Q Casi >‘:__."'"'< ‘E"?M§a g3 )Cgfia “w $3 Q C 5: G W >---* ' s s 53;; a ’_\ u a 13 QM % 2. Compare all of the CO bond lengths in the three species. fi‘g methanol, CHSOH carbon dioxi e, CO2 bicarbonate HCO; Q5 lows smeg r” . . 25a is E ' O i " I / s ,. , ' H L : at ‘5 s. a K a a a H / \ C. l «HQ 973% g / \ngi 3%, 35> / a, a x? 3. Draw the Lewis structure for CHZNH and, build a model of it. Are all of the in the same plane? , ' - o ‘ s. Draw an orbital overlap diagram (show sigma and pi bonds as orbital overlaps)?M dz {Rama‘f‘g " . r 5i é¥a35~s lgmé his «was §\ 5 / Q53 AK g? 5%» 4. Draw the Lewis structure for CHZCNH and build a model of it. Are all of the% in the same plane (Note the dzfi‘erence in the formula for this compound and the one in number 3!) W§ f Draw an orbital overlap diagram (show sigma and pi bonds as orbital overlaps). 4 WWW»WW 5. Consider the structure below and answer the following questions. \1 :—<———-oo --nm|O I A) Assuming all atoms depicted have a complete octet, write in formal charges on those atoms that have a charge as depicted in this Lewis structure. (Hint: Putting in the lone pairs may help you.) s I 5306qu B) What is the overall charge on the molecule? C) OMIT D) What is the hybridization on the following atoms? 9c N-1O = 5E N-12 = 5 0-8 x 3 c 9 - 3» O4: égf‘ 07: Sf 3 QB :33 E) What are the following approximate bond angles about the central atoms specified? N—10=, logasb N~12= :30" 0—8: “MEQSO C—2= lgop c-3= lO‘ng’ C—5= 5205 C-6= {C609 c—11=IO?.S° F) What is the shape with respect to the following central atoms? N—lz N—10= ZET N—12: EL c—2=Tl> C-4 = G7 = 757 0-8 = B 09 = TET L = Linear B = Bent PL = Trigonal Planar TET = Tetrahedral PYR = Trigonal Pyramidal G) Circle portions of the molecule that will have pi—deloca-lization of electrons (over 3 or more atoms) ...
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