Exams_exam_2_answers - Chemistry 239 Autumn 2005 Exam 2 ‘ Answer Key Student#1 Your name V Sign here to indicate your approval of public return

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Unformatted text preview: Chemistry 239 Autumn, 2005 Exam 2 ‘ Answer Key Student #1 Your name: V Sign here to indicate your approval of- public return of your paper: _ 1 (18 pts.) Give structures or names for the compounds below. _ CH3CH2CH2CO$HCOZCH3 ' CH3CH2 methyl Z-ethyI-S-oxohexanoate' N-n'itrosomethyiamine pyridine cyclohexyianil'ine or .tphenylcyclohexanamine methyldiazonium ion 1 ‘ show all bonds, unbon‘debd electrons, formal charges CH3NHNQ ‘ anion from the reaction of ' chlorobenzene with amide anion 2 (5 pts.) Complete a balanced equation for a proton transfer between the reactants below, label the stronger and weaker acids involved, indicate whether the position of equilibrium is favorable (to the right) or unfavorable (to the left) and suggest a reason why. a Hoiqu2 + CH3NH3+ weaker acid [pKA == stronger acid [pKA = 6.0] unfavorable electronegative oxygeninductively ' destabilizes positive charge Chem 239 Autumn, 2005 Exam 2 Answer Key p. 2 3 (28 pts.) In the reactions below fill in the missing items (starting materia1[s], reagents and conditions over the arrow, or main organic product[s]). o ' v 1- M303 0 OCOOCH3 \ engococoom3 O ~————-————> O 2. H30+ I 1. EtO' O\ /0 W’ 2. H3 + H3 C“3 0 C 1. EtO‘ 2. Br(CH2)4Br C(COZCHZCH3)2 —--—--———-———> - CH3Br . P_hN(CH3)z ——————» PhN(CH3)3+,Br’ Ns' H2. cat or 1. LiAIH4, 2. H20 Ph(CH2)zBr Ph(CH2)2N3 ——————~—————————> Ph(CH2)2NH2 'Fe, HCI ~ HNOZ, 0°C p C|_c6H4_N02 -~————> p CI-C5H4-NH2 “H p C|--C(5H4-N2+ O 1. LiAlH4, 2. H20 CH3 N-CH3 ——-—-—~———> CHgCN-CH3 CH3‘©‘ NHz WW? ' Chem 239 Autumn, 2005 Exam 2 Answer Key p. 3 4 (10 pts.) Draw a curved arrow mechanism for the reaction you would expect‘for the decomposition of the 2—methylpropy1 diazonium ion in water to form an alcohol. (Show all unpaired electrons and formal charges.) H +| Me3C-O-H + H—-o—H for a compound I . a) I had a molecular ion in peak its mass spectrum at m/z = 1 16. b) Theacompound I was basic, and its IR spectrum showed no peaks between 3300—3 500 cm“. c) I gave the nmr spectrum below — show your peak assignments and label the multiplicity of all peaks. H.“ b) tertiary amine [C6H16N2=72 + + = Chem 239 . Autumn, 2005 Exam 2 Answer Key p. 4 mmWamm= 6 (10 pts} Show how you would carry out the synthesis below. (Show the main product after each step, with reagents and any special conditions over each reaction arrow.) from CH3CH2C02CH2CH3 :' 1:. EtO’“ g 2:336? ' " ” _ _ -- ' ' -. - * Cheffl Autumn, 2005 Exam 2 ~ Answer Key p. 5 8 (9 33th} For the qtiaternary ammonium ion below, a) Show the major alkene you would expect to be formed upon eliminatiOn (heating) OH”, heat W + N(CH3)3 b) Draw Newman projections of the conformations leading to the two competing transition states in this reaction, and use them to explain why the pathway you chose is favored. \/\/‘ Me Me JJJ+ NMe3H ‘ more hindrance less hindrance favored pathway ...
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This test prep was uploaded on 04/15/2008 for the course CHEM 239 taught by Professor Sasaki during the Spring '06 term at University of Washington.

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Exams_exam_2_answers - Chemistry 239 Autumn 2005 Exam 2 ‘ Answer Key Student#1 Your name V Sign here to indicate your approval of public return

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