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Chem_62_Exam_Key_2_9_06

Chem_62_Exam_Key_2_9_06 - V Short AnswerIMultiple Choice(18...

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Unformatted text preview: V. Short AnswerIMultiple Choice. (18 pts) 1. Which of the foliowing is true of the methoxy (CH30) group in the following reaction? CH Cl, MCI ~an ——3—3—- H.300... A. The methoxy group is donating by induction and withdrawing by resonance. B. The methoxy groupie withdrawing by resonance and induction. C. The methoxy group is donating by induction and resonance. The methoxy group is donating by resonanm and withdrawing by induction. 2. Number the following compounds from the least acidic (#1) to the most acidic (#4). CH3 .Q.. .011,“ d; .0... 3 l Ll Q. 3. In the aromatic compounds, pyridine (A) and pyrrole (B), shown below, in what orbital is the lone pair on the nitrogen found in each compound? A. /| B. {J ‘- N N H 2p: -P— 4. Circle the compound(s) that is (are) aromatic. A. Y .9 c. Q o. C) '6 5. Circle the name of the mechanism that accounts for the following reaction. 0—0” _ mm 00% NaOH, H20. CHZCIZ, BU4N+ Br' A. Nucleophilic Aromatic Substitution B. Substitution Nucleophilic Unimolecular © Substitution Nudeophilic Bimolecular 0. Phase Transfer Catalysis B. II II Hac-CQF NaOH H30 4: Q—OH + NaF N CN 0 i1 0 0 {90“ E30 0 ‘I 0 “ ’ 9' __ “fig; e—e up F 4-7 “£9 F “Amp?” ) L3,, GEN LQJS (fin 9:5: \4 l Hzc'csg; a '3“ can “5°C“ F i'\ 0% o "‘ Rare" a: *5 .w o' ¢=u c- IV. Synthesis. Wtite the starting meterie|(s), the reagenqs) and the prodmfls) for each of thereaefionsnecesearytogetfmmthestarling matefialtofl'ieproduet. Numbereech reaction. No mechanism is necessary! (20 pts.) ' '30“; an?) ‘2- PfaC-U‘Oq ‘13. 599'} [W04 or chr'qu. F9 0 01.3ng / HO E_ 6 1. ‘1 Nomad a. H9 F ‘ , NM H. “1.0 I Q Q. was @001.)qu r (Ll—1,14 or“ A OH Cl III. Write a detailed stepwise mechanism for the following reactions. Include §_ll_important resonance structures. (20 pts) Cl Honor Code: I have neither given nor received unauthorized aid on this exam. i understand that I am not allowed to use any calcuiator. notes. books. or resources (other than molecular models). I also understandihat removal ofthe examfrom thetesting room orreoeiving aidfnom any other person orotherperson‘sexamoonstitutesan honoroodeviolation. Ialsounderstandthat making any change to an exam answer post—grading with the intent of submission for regrading is an honor code violation. Signature: A3 M la,= % PID# Please clearly print your last name: Chemistry 62 (Spring 06) Exam 1 A511”? PL I. Nomenclature (13 points) 19fo Pt. II. Reactions _ _.._. _. (24 poims) ‘ja k2,. Pt. I", Mechanisms ______(20 points) Mi Clam Pt. Iv. Synthesis _(20 points) fl Qabé’mfi Pt. v. Short Ans. __________(18 points) W TOTAL __ (100 point!) ...
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