CHEM 234, Spring 2016 COMPLETE THIS SECTION : Up to TWO POINTS will be removed for incorrect/missing information!
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1 EM 234, Spring 2016 FIAL EXAM MPLETE TIS SETI : Up to TW PITS will be removed for incorrect/missing information! Ian R. Gould PRITED FIRST AME PRITED LAST AME a Mg Person on your LEFT (or Empty or Aisle) Person on your RIGT (or Empty or Aisle) **YU ARE T ALLWED T TAKE SPARE PIES F TIS EXAM FRM TE TESTIG RM** 1 /12 10 /40 PRIT YUR AME EA PAGE! 2 /20 11 /30 READ TE DIRETIS AREFULLY! 3 /20 USE BLAK PAGES AS SRAT PAPER 12 /35 4 /10 work on blank pages will not be graded /40 5 /20 WRITE LEARLY! 14 /20 MLEULAR MDELS ARE ALLWED 6 /24 15 /8 D T USE RED IK 7 /72 Points Removed (cover errors) /2 D'T EAT, USE MM SESE! 8 /8 Extra redit /5 9 /16 Total (incl Extr /175+5 e Li Be B F e Interaction Energies, kcal/mol Al Si P S l Ar K a Sc Ti V r Mn Fe o i u Zn Ga Ge As Se Br Kr Rb Sr Y Zr b Mo Tc Ru Rh Pd Ag d In Sn Sb Te I s Ba Lu f Ta W Re s Ir Pt Au g Tl Pb Bi Po At Rn R 2 R (δ, ppm) variable and condition dependent, ca. 2-6 δ R R ASU or Posting ID lass you are REGISTERED FR (onground or hybrid) Room you would take this test in if you were in class (LS A-191 for onground and PS -152 for hybrid) Aromatic R 2 R 2 Xe R 2 Aromatic Ar mainly R Eclipsing / ~1.0 /Me ~1.4 Me/Me ~2.6 Me/Et ~2.9 Infrared orrelation hart small range usually range of values strong broad peak peaks R 2200 broad with spikes ~ broad ~ broad ~ R (cm -1 ) 1500 MR orrelation harts 2 X R R 2 R Gauche Me/Me ~0.9 Et/Me ~0.95 i-pr/me ~1.1 t-bu/me ~2.7 Alkyl X Alkyl 3 > 2 > > 2 > 1 0 0
2 M 234, Spring 2016, FIAL EXAM AME Question 1 (12 pts.) Provide a IUPA name for the following structure, do not forget to use E/Z and R/S as appropriate. Br Question 2 (20 pts) Rank the following in order of increasing Bronsted acidity, and provide a BRIEF explanation. You MUST draw the structures of ALL F the conjugate base anions including ALL reasonable resonance contributors A B < < weakest strongest Extra redit Question (5 pts). What kind of functional group is hydrolyzed to form soap? carboxylic acid ester amide aldehyde
3 M 234, Spring 2016 FIAL EXAM -3 - AME Question 3 (20 pts.) For the following acid/base equilibrium: draw the curved arrows showing bond making/breaking b) indicate which is the STRGER and the WEAKER acid and base on each side c) give a BRIEF explanation for your choice of stronger/weaker that includes the phrase "energy of the electrons" + + d) Indicate which reaction (left to right or right to left) is faster and which is slower and indicate on which side the equilibrium lies e) Draw a PRPERLY labelled reaction energy diagram, indicate the position of the transition state and include a drawing of the transition state Question 4 (10 pts.) Rank in order of increasing equilibrium constant for formation of a hydrate. Give a BRIEF explanation. A B < < smallest largest
4 M 234, Spring 2016, FIAL EXAM AME Question 5. (20 pts.) Give a curved arrow-pushing mechanism for the reduction of the provided ester to butanol and methanol. You must draw the Lewis structure of the Al 4 anion and you MUST show exactly where each proton comes from and goes to here, no ++ and -+ notation, and you must also show how the methanol is formed. Me 1. LiAl Me Question 6 (24 pts.) For the reaction between structures A and B below, you are going to determine whether the PRVIDED product is allowed or forbidden, using F.M.. theory. Draw the curved arrow-pushing that describes the bond-making and breaking processes. D D Me Me Δ Me + Me Me D A B D Me b) Was the PRVIDED PRDUT (which may or may not be allowed) formed via suprafacial or antarafacial reaction for reactant A? c) Was the PRVIDED PRDUT (which may or may not be allowed) formed via suprafacial or antarafacial reaction for reactant B? d) Draw the M for A and the LUM for B on TP of the structures that are redrawn for you below, for EA, give the number of vertical nodes Me D D Me Me # vertical nodes = # vertical nodes = M for A LUM for B e) Is the cycloaddition reaction shown above allowed or forbidden. Give a BRIEF explanation that includes the words "suprafacial" and/or "antarafacial" as appropriate
5 M 234, Spring 2016, FIAL EXAM AME Question 7 (72 pts) Provide the missing major organic products for the following reactions. Do not forget to include stereochemistry as appropriate and IDIATE AY RAEMI MIXTURES. heat (electrocyclic ring closure reaction) b) 1. Excess PhMgBr c) 2 S 4 d) 2 Ph l 1 equivalent Br 1. Mg. TF e) (ignore stereochemistry for this problem) 2 f) + F 3 heat F 3
6 M 234, Spring 2016 FIAL EXAM AME Question 7, ontd... Provide the missing major organic products for the following reactions. Do not forget to include stereochemistry as appropriate and IDIATE AY RAEMI MIXTURES. h) 2 1. Excess MeI 2. Ag 2 /heat (ignore stereochemistry for this problem) 1. a + - Me/Me i) Ph + Ph Me excess (ignore stereochemistry for this problem) j) + excess Ts cat. / heat Question 8 (8 pts) Give all reactants/reagents and conditions that would be used to give the provided structure below. Indicate whether the reaction is a Aldol reaction or a laisen reaction. ignore stereochemistry Me Question 9 (16 pts.) I TE BXES, give the missing reagents/conditions or structures, as required, to complete the following Stork (enamine) alkylation of cyclopentanone give reagents give reagents give structure give reagents Ph
7 EMISTRY 234, Spring 2016 FIAL EXAM AME Question 10 (40 pts.) Show how you would make the target componds on the right from the starting compounds on the left. Show reagents and conditions where appropriate, and the structures of important intermediate compounds. Do not show any (arrow pushing) mechanisms. If necessary, you must indicate steps that require separation of isomers l Br 2 These questions use only reactions from the "minimal" sets that were provided on the class website b) (ignore stereochemistry) c) Br Ph
8 EMISTRY 234, Spring 2015 FIAL EXAM AME Question 11 (30 pts.) Give a curved arrow-pushing mechanism for the following reaction Show where all protons come from and go to (no + + /- + ) Show all resonance contributors to the intermediate structures Label the Lewis acid/base and and Bronsted acids/bases as appropriate 3 + b) 2 /a
9 M 234, Spring 2016, Final Exam AME Question 12 (35 pts). Give a curved arrow pushing mechanisms for the following two reactions. 1) Add non-bonding electrons and - bonds to the line-angle structures as required. 2) Indicate the Lewis acid/lewis base (LA, LB) at each ITERMLEULAR step as appropriate, and whether they are also Brønsted acids/bases (LA/BA, LB,BB) 3) YU D T AVE T DRAW RESAE TRIBUTRS for intermediates 4) GIVE TE UMBER F STEPS I YUR MEAISMS 5) Show where ALL protons come form and go to, no abbreviated + + /- + notation 3 + eat + b) a + Et Et Et
10 M 234, Spring 2016 FIAL EXAM AME Question 13 (40 pts.) Show how you would make the target componds on the right from the starting compounds on the left. Show reagents and conditions where appropriate, and the structures of important intermediate compounds. Do not show any (arrow pushing) mechanisms. dopamine 2 b) Ph
11 M 234, Spring 2016 FIAL EXAM AME Question 14 (20 pts.) Synthesize the (target) molecule on the right from the starting molecule the left. this can not be done in one reaction. Give reagents and conditions and the intermediate molecules at each step. Do not show any mechanisms or transient intermediates. Ignore stereochemistry! Br Question 15 (8 pts.) Give the structure of the ketone and ALL TER reagents/conditions you would use to synthesize amphetamine via a reductive amination 2 amphetamine
**YOU ARE NOT ALLOWED TO TAKE SPARE COPIES OF THIS EXAM FROM THE TESTING ROOM**
EM 234, Spring 2018 Final Exam Ian R. Gould MPLETE TIS SETI : Up to TW PITS will be removed for incorrect/missing information! PRITED FIRST AME PRITED LAST AME Person on your LEFT (or Empty or Aisle) Person
More information**YOU ARE NOT ALLOWED TO TAKE SPARE COPIES OF THIS EXAM FROM THE TESTING ROOM**
EM 234, Spring 2017 Midterm #3 Ian R. Gould MPLETE TIS SETI : Up to TW PITS will be removed for incorrect/missing information! PRITED FIRST AME Answer Key Person on your LEFT (or Empty or Aisle) Person
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EM 234, Spring 2008 PRITED FIRST AME PRITED LAST AME Final Exam ASU ID or Posting ID Ian R. Gould Person on your LEFT (or Aisle)!PRIT YUR AME EA PAGE! READ TE DIRETIS AREFULLY! USE BLAK PAGES AS SRAT PAPER
More informationFinal Exam ASU ID or Posting ID 8 /18... Extra Credit /5
EM 234, Spring 2008 PRITED FIRST AME PRITED LAST AME Final Exam ASU ID or Posting ID Ian R. Gould Person on your LEFT (or Aisle)!PRIT YUR AME EA PAGE! READ TE DIRETIS AREFULLY! USE BLAK PAGES AS SRAT PAPER
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EM 234, Spring 2010 PRITED FIRST AME PRITED LAST AME Second Midterm ASU ID or Posting ID Ian R. Gould Person on your LEFT (or Aisle) PRIT YUR AME EA PAGE! READ TE DIRETIS AREFULLY! USE BLAK PAGES AS SRAT
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EM 234 PRITED FIRST AME the exam cover sheets look kind of like this PRITED LAST AME ASU ID or Posting ID Ian R. Gould Person on your LEFT (or Aisle) Person on your RIGT (or Aisle) PRIT YUR AME EA PAGE!
More information**YOU ARE NOT ALLOWED TO TAKE SPARE COPIES OF THIS EXAM FROM THE TESTING ROOM**
EM 233, Fall 2016 Midterm #3 Ian R. Gould MPLETE TIS SETI : Up to TW PITS will be removed for incorrect/missing information! PRITED FIRST AME Answer Key Person on your LEFT (or Empty or Aisle) Person on
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EM 234, Spring 2018 Final Exam Ian R. Gould MPLETE TIS SETI : Up to TW PITS will be removed for incorrect/missing information! PRITED FIRST AME Answer Key Person on your LEFT (or Empty or Aisle) Person
More informationThird Midterm EAS 2 /15... Keq 3 /12... Stork 4 /14... Retro 6 /38... Benene R 7 /20... Claisen Mxn 8 /20... Extra Credit /5
EM 234, Spring 2008 PRITED FIRST AME PRITED LAST AME Third Midterm ASU ID or Posting ID Ian R. Gould Person on your LEFT (or Aisle)!PRIT YUR AME EA PAGE! READ TE DIRETIS AREFULLY! USE BLAK PAGES AS SRAT
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HEM 234, Spring 2017 Midterm #2 Ian R. Gould MPLETE THIS SETIN : Up to TW PINTS will be removed for incorrect/missing information! PRINTED FIRST NAME PRINTED LAST NAME Person on your LEFT (or Empty or
More informationCHEM 234, Spring 2015 PRINTED FIRST NAME. Final Exam ASU ID or Posting ID. Ian R. Gould PRINTED LAST NAME
CEM 234, Spring 2015 PRINTED FIRST NAME PRINTED LAST NAME Final Exam ASU ID or Posting ID Ian R. Gould Person on your LEFT (or Aisle) Person on your RIGT (or Aisle) 1 /12 2 /20 3 /25 4 /12 5 /20 6 /64
More informationFirst Midterm. Ian R. Gould PRINTED FIRST NAME. noman 2 /17 1 /10. acidity 3 /39. reactions 4 /21. bonds 5 /12. acidity 2 6 /40. synth 7 /36.
EM 234, Spring 2011 First Midterm Ian R. Gould PRITED FIRST AME ASWER PRITED LAST AME KEY ASU ID or Posting ID Person on your LEFT (or Aisle) PRIT YUR AME EA PAGE! READ TE DIRETIS AREFULLY! USE BLAK PAGES
More informationThird Midterm. Witig 2 /18... reactions 3 /32... retro 1 4 /40... mxn 1 6 /20... max 2 7 /15... Extra Credit /5. Infrared Correlation Chart C O
EM 234, Spring 2009 Third Midterm Ian R. Gould PRITED FIRST AME ASWER PRITED LAST AME KEY ASU ID or Posting ID Person on your LEFT (or Aisle)!PRIT YUR AME EA PAGE! READ TE DIRETIS AREFULLY! USE BLAK PAGES
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EM 24, Spring 2017 Midterm #2 Ian R. Gould MPLETE TIS SETIN : Up to TW PINTS will be removed for incorrect/missing information! PRINTED FIRST Answer Key Person on your LEFT (or Empty or Aisle) Person on
More informationMidterm #2 PRINTED LAST NAME 2 /20 3 /16 4 /9 5 /8 7 /24
EM 234, Spring 2016 PRINTED FIRST complete this section ANSWER KEY Midterm #2 PRINTED LAST Ian R. Gould Person on your LEFT (or Empty or Aisle) Person on your RIGT (or Empty or Aisle) ASU or Posting ID
More informationCOMPLETE THIS SECTION : Up to TWO POINTS will be removed for incorrect/missing information!
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EM 233, Spring 2016 Midterm #1 MPLETE TIS SETI : Up to TW PITS will be removed for incorrect/missing information! Ian R. Gould PRITED FIRST ME PRITED LST ME Person on your LEFT (or Empty or isle) Person
More informationFinal Exam. Ian R. Gould PRINTED FIRST NAME
CEM 234, Spring 2015 Final Exam Ian R. Gould PRITED FIRST AME ASWER PRITED LAST AME KEY ASU ID or Posting ID Person on your LEFT (or Aisle) Person on your RIGT (or Aisle) 1 /12 2 /20 3 /25 4 /12 5 /20
More informationCHEM 233, Spring 2016 COMPLETE THIS SECTION : Up to TWO POINTS will be removed for incorrect/missing information!
EM 233, Spring 2016 Midterm #1 MPLETE TIS SETI : Up to TW PITS will be removed for incorrect/missing information! SWER KEY PRITED FIRST ME PRITED LST ME Ian R. Gould Person on your LEFT (or Empty or isle)
More informationMidterm #1. key 1 / / / / / / /14... Extra Credit /5. Infrared Correlation Chart. NMR Correlation Charts
EM 233, Fall 2015 PRITED FIRST AME answer PRITED LAST AME Midterm #1 key ASU ID or Posting ID Ian R. Gould Person on your LEFT (or Aisle) PRIT YUR AME EA PAGE! READ TE DIRETIS AREFULLY! USE BLAK PAGES
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EM 233, Fall 2017 Midterm #2 Ian R. Gould MPLETE TIS SETIN : Up to TW PINTS will be removed for incorrect/missing information! PRINTED FIRST PRINTED LAST Person on your LEFT (or Empty or Aisle) Person
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EM 233, Fall 2017 Midterm #3 Ian R. Gould MPLETE TIS SETIN : Up to TW PINTS will be removed for incorrect/missing information! PRINTED FIRST NME answer key PRINTED LST NME Person on your LEFT (or Empty
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EM 234, Spring 2011 Second Midterm Ian R. Gould PRITE FIRST ME SWER PRITE LST ME KEY SU I or Posting I Person on your LEFT (or isle) PRIT YUR ME E PGE! RE TE IRETIS REFULLY! USE LK PGES S SRT PPER work
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EM 233, Fall 2018 Midterm #1 Ian R. Gould MPLETE TIS SETI : Up to TW PITS will be removed for incorrect/missing information! PRITED FIRST ME nswer Key ME F the Person on your LEFT (or Empty or isle) ME
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