Exam1_Key

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Columbia University *

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C3443

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Chemistry

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Oct 30, 2023

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pdf

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7

Uploaded by DeanDanger11932

LAST name: I‘\/P W First letter of your last name First name: CUID:, Organic Chemistry | CHEM C3443 Exam 1 On my honor, | have not given or received help on this examination. Signature Fall 2012 September 25 Page 2: n2 Page 3 120 Page 4: s Page 5: 21 Page 6: 120 Page 7: n2 Total: -In addition to this document, all you need is a pencil (or a pen) and an eraser. -ALL OTHER ITEMS SHOULD BE TURNED OFF AND PUT AWAY. -This document contains a total of 7 pages. CHECK that you have all in this packet. -Write your name on every page. -Write your answers clearly and concisely on the space provided. -Use the blank pages to work through the problems, but they will not be graded. -Raise your hand to request scratch paper. -You will also receive a periodic table Good Luck!!!
Name: 1.6 pts. a. Draw the molecular orbital picture of the methyl cation (*CHs) and label all molecular o and = bonds, where necessary, and any non-bonding atomic orbitals (s, p, etc). b. What is the hybridization of the carbon atom? S PL 60 g ak) ond c,- vl el i, e’ <@ s ) k) 2. 6 pts. Draw the Lewis dot structures of SO, and NO>, and specify the formal charge at each atom, if any (no need to specify formal charge of zero). Your answer must be in the box. S0, NO, pts. this pg
Name: 3a. 5 pts. Consider the molecule drawn in box A below (methyl acetate). Add the lone pairs where necessary. In box B, draw its resonance structure (make sure that all octets are filled, don't forget to add the lone pairssand charges). Draw the curly arrows that show the movement of electrons betweetructures in Aand B. resonance structure. o pts. To the amide shown below, apply the same analysis as above to boxes C and D. - Z\:d' D '6'9 HSC)J\l/iI\)I'/CHS e %k\/%/ CHy L resonance structure 3b. 10 pts. The C-X single-bond (where X = C, O, or N) in bold allows for rotation. In the series shown below, the rotation energy barrier is listed for each molecule. Briefly justify the observed trend. o I} 1l H,c-GcH3 P /c{(:‘ > Barrier to | rotation 3 keal/mol 11 kcal/mol 16 kcal/mol - The karrier fo lation in ;—\—\'\mwe is amall becavse £ woese shaoye Eowmd withou + any steric Whea chions | - The barriers are L\lb‘f\&r v A& C decauvse Hre wsoaan e chruchores cliowm 1 oxes B é\) sbows the double bowd charmcler that exists W Hhese wole cules setwen the bonds n q_ged-lw ~ The baedier is Lishey in $uaw A becuvse Yo resovance Sruchure D) is wove m(e\s *—o(c«vr\) o gosiHue p_\m;.rb& ia the @V]Efio ", mmy«mcxl to ?lm_'vsq ?os;'iiu? c(/nry ov Ox\Muen in R, “this leads Yo signi Gcant wore contribution e TSN ANEL, 10 Strocture VY W GBI 3 (<>D.
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