Third Midterm EAS 2 /15... Keq 3 /12... Stork 4 /14... Retro 6 /38... Benene R 7 /20... Claisen Mxn 8 /20... Extra Credit /5
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1 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 PAPER work on blank pages will not be graded... WRITE LEARLY! MLEULAR MDELS ARE ALLWED D T USE RED IK D'T EAT, USE MM SESE! Li Be B F e a Mg e 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 (cm -1 ) amine alcohol (!, ppm) small range range of values broad peak R 2 R R R variable and condition dependent, ca. 2-6! peaks Aromatic Ar mainly usually strong Person on your RIGT (or Aisle) 1 /9 nomen...9 /20... Mxn 2 /15... EAS 3 /12... Keq 4 /14... Stork 5 /32 Reactions... 6 /38... Retro 7 /20... Benene R 8 /20... laisen Mxn Extra redit / R R 2 R Xe Infrared orrelation hart Total (incl Extra) / R Interaction Energies, kcal/mol Eclipsing / ~1.0 /Me ~1.4 Me/Me ~2.6 Me/Et ~ R broad with spikes ~ broad ~ R2 broad ~ MR orrelation harts X R 2 R X Gauche Me/Me ~0.9 Et/Me ~0.95 i-pr/me ~1.1 t-bu/me ~2.7 Approximate oupling onstants, J (z), for 1 MR Spectra Alkyl 3 Y > 2 Y > 1 Y Alkyl ~10 ~2 ~ ~8 ~2 ~ Y > 2 Y > 1 Y Aromatic R 2
2 M 234, Spring 2008, Midterm #3-2 - AME Question 1 (9 pts.) Give an unambiguous IUPA or common name for the following compounds. Be sure to use cis/trans, E/Z or R/S where appropriate. [6S]-hydroxy-2-methyloct-1-en-4-one Question 2 (15 pts). Rank in order of increasing rate of electrophilic aromatic substitution at the carbons indicated by the arrows. Give a BRIEF explanation. B A 3 B < < A slowest fastest Reaction at both A and is faster than at B, because both are activated by strong (amine) and weak (aryl) donating groups on the ring. Reaction at A is activated more than at because the donating group stabilizes the intermediate more at this position it is o- and p-directing). Reaction at B is deactivated by the by the strongly withdrawing nitrile group.
3 M 234, Spring 2008, Midterm #3-3 - AME Question 3 (12 pts). a) Rank the following reactions in order of increasing equilibrium constant for formation of product and give a BRIEF explanation A l cat. A smallest < < B largest B l cat. l cat. as far as the = is concerned, the in A is strongly donating which decreases reactivity, the in B is mildly withdrawing due to the inductive effect which increases reactivity, in the effect is negligible and the alkyl groups are weakly donating, intermdiate reactivity Question 4 (14 pts) In the boxes, fill in the missing reagents/conditions in the following reaction sequence + Br cat. (not 3 + ) 3 +
4 M 234, Spring 2008, Midterm #3-4 - AME Question 5 (32 pts.) provide the reaction products or reagents/conditions as required a) 1. Et + a/ Et Et b) 2 l (cat.) c) Zn/g l/ 2 d) S S 1. BuLi 2. 3 Br 3. BuLi Br
5 M 234, Spring 2008, Midterm #3-5 - AME Question 6 (38 pts.) In each case, synthesize the (target) molecules on the right from the starting molecules 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. a) BS/h! Ph 3 P 2 Br K + -t-bu 1. g(ac) 2 / 2 2. ab 4 P b) Ph 1 Equiv EtMgBr Ph Ph K/heat Ph 3 +
6 M 234, Spring 2008, Midterm #3-6 - AME Question 7 (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. 2 2 l All 3 S 3 1. KMn 4 / /boil S 3 / 2 S 4 2 Zn(g) 3 l/ 2 2 S 4 S 3 S 3 S 3 Extra credit question (5 pts). A photochemical cycloaddition reaction occurs in DA emoglobin Vitamin peroxidase from weekly work #12
7 M 234, Spring 2008, Midterm #3-7 - AME Question 8 (20 pts.) Give a complete arrow-pushing mechanism for the following TW reactions. Show exactly where each proton comes from and goes to. Add non-bonding electrons and hydrogen atoms as necessary Indicate the lewis acid/base for each ITERmolecular step (LB or LA) and whether they are also Brønsted bases/acids (LB/BB or LA/BA) SW ALL RESAE STRUTURES F TE ITERMEDIATES 3 1. a + 3 /
8 M 234, Spring 2008, Midterm #3-8 - AME Question 9 (20 pts.) Give a complete arrow-pushing mechanism for the following reaction. Show exactly where each proton comes from and goes to. Add non-bonding electrons and hydrogen atoms as necessary Indicate the lewis acid/base for each ITERmolecular step (LB or LA) and whether they are also Brønsted bases/acids (LB/BB or LA/BA) SW ALL RESAE TRIBUTRS F TE ITERMEDIATES LB 2 LA l (cat.) l LA/BA LB/BB l LA/BA l LB/BB LA/BA LB/BB LA/BA l LB/BB 2
Third 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
More informationMIDTERM #3 PRACTICE TEST #1
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 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 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
More informationFinal Exam ASU ID or Posting ID
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 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, 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)
More information**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
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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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More informationCOMPLETE THIS SECTION : Up to TWO POINTS will be removed for incorrect/missing information!
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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
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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
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