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CHEMISTRY ORGANIC 30C (Prof. Yves Rubin) UCLA, FALL 2007 MIDTERM EXAM II On my honor, I have neither given nor received any aid on this exam (Please, use ink for this first page!): ____________________________ Signature __________________________ I. D. Number ____________________________ Full Name (Please Print !) Question 1 (25) 2 (25) 3 (25) 4 (25) Total (100) Points ========= Organic Chemistry 30C Fall 2007 EXAM 2, Page 1 I. CONCEPTS AND THEORY __________________ Name 1. a) (10 points) The following compound reacts unusually fast with up to 3 equivalents of bromine in H2O at 25 C under basic conditions. Explain this unusual reactivity (not the selectivity) using resonance arguments: OH 1) 3 eq. Br2, 4 eq. NaOH H2O 2) H3O+ workup Br OH Br Br b) (5 points) Draw relative energies for the molecular orbitals (MOs) of the cyclobutadiene dication shown below. Indicate in which MOs the electrons are located and predict its stability: 2+ c) (10 points) Give the total number of -conjugated electrons and determine whether the following compounds should show aromatic, antiaromatic, or non-aromatic character (you can show charged resonance structures if helpful): O N NMe O N H N+ electrons: ___________ Character: ___________ ___________ ___________ ___________ ___________ ___________ ___________ ___________ ___________ Organic Chemistry 30C Fall 2007 EXAM 2, Page 2 II. REACTIONS __________________ Name 2. (25 points) Give the major product for the following reactions, assuming 1 equivalent of reagent is used unless specified otherwise (show each step, applicable, where to ensure max. credit if you are not sure of your final product): a) 1) Cl2, FeCl3 2) Br2, FeBr3 OMe b) 1) Br2, Fe 2) HNO3, H2SO4 3) Cl2, Fe 4) CH3COCl, AlCl3 c) 1) Br2, Fe 2) NaBH4 3) H+, heat O d) OOO 1) , AlCl3 then H3O+ workup 2) Zn(Hg), HCl 3) SOCl2 3) AlCl3, then H3O+ Organic Chemistry 30C Fall 2007 EXAM 2, Page 3 III. MECHANISMS __________________ Name 3. (25 points) Provide a complete, detailed mechanism with curved arrow formalism for the following reactions. Each step must me explicitly written down, i.e. every attack of reagent, bond breaking and bond forming steps must be shown! a) (15 points) Show two key resonance structures for each of the two pathways below and also explain which pathway is most favorable and why. OMe OMe Br2 Br OMe Br2 Br (10 points) Explain why the following reaction is not expected to give just a single product (give a simple answer, use mechanisms as your argument): Me CH3CH2CH2CH2Cl, AlCl3 Organic Chemistry 30C Fall 2007 EXAM 2, Page 4 IV. TRANSFORM __________________ Name 4. (25 points) Devise a reasonable synthesis for each of the following compounds from reagents you are familiar with and the starting materials provided: Note: do no invent new reagents or reactions. Use only those specifically taught in class or in previous quarters. There should not be more than 10 steps necessary in these syntheses, although longer ones may also be correct. a) (15 points) Cl Br CH2CH2CH2CH3 Cl Organic Chemistry 30C Fall 2007 EXAM 2, Page 5 __________________ Name 4. b) (10 points) Br Br NO2
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UCLA >> CHEM >> 30c (Winter, 2008)
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UCLA >> CHEM >> 30c (Winter, 2008)
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UCLA >> CHEM >> 30c (Winter, 2008)
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UCLA >> CHEM >> 30c (Winter, 2008)
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UCLA >> CHEM >> 30c (Winter, 2008)
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UCLA >> CHEM >> 30c (Winter, 2008)
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UCLA >> CHEM >> 30c (Winter, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
Practice Problems for Chemical Kinetics 2 MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) The reaction A + B C + D is second order in A and zero order in B. The value of k is 0.012 M-1 min-1 ....
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
Solids and Crystals Pratice Problems MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Which of the following is considered an atomic solid? A) N2 B) CsCl C) Nb D) Br2 E) None of these is an ato...
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
Solutions Practice Problems 1) In a solution, the solvent A) is always a liquid. B) is either liquid or gas. C) is always the substance present in the largest concentration. D) is never the substance present in the smallest concentration. E) can be a...
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
Practice Problems for Proteins 1) What is the isoelectric point for an amino acid or polypeptide. 2) What atoms define the and angles of a peptide? 3) Draw the structure of a tripeptide, labelling the sidechains as \'R\'. Label the bonds that are d...
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
What is the breakdown in % on the final of old material and new? Will the format be the same as our previous tests? (should I bring the same scantron?) Do we need a calculator for the final? The final is ~50% cumulative and ~50% non-cumulative - sam...
UCLA >> CHEM >> 89 (Fall, 2008)
1 (1A) 1 Periodic Table of the Elements 13 (3A) 14 (4A) 15 (5A) 16 (6A) 17 (7A) 2 18 (8A) 1 H 1.008 3 4 Atomic number Elemental symbol Atomic mass He 4.003 80 5 6 7 8 9 10 2 Li 6.941 11 Be 9.012 12 200.59 Liquid at 25 C Zn Solid at 25 ...
UCLA >> CHEM >> 89 (Fall, 2008)
Spontaneity and free energy practice problems 1 1) How can energy be transferred to or from a system? A) Energy can be transferred as potential energy, which must be converted to kinetic energy. B) Energy can be transferred only as heat. C) Energy c...
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
Chemistry1ASection1196 GeneralChemistryI Fall2008 Instructor:Dr.PeterA.Doucette email:pdoucette@elcamino.edu OfficeHours:TBA Meetingtimesandlocations: Lectures: Labs: TTh M W 2:004:05 1:004:10 2:054:10 Chem103 C...
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
Practice problems for acids and bases 1 MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) According to Bronsted and Lowry, what is the definition of a base? A) A base is an electron pair donor i...
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
Solids and liquids practice problems 1) Which of the following is a true statement concerning water? A) The predominant force between water molecules is dispersion force. B) The water molecule has a molecular dipole that points toward its hydrogen a...
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
Stoichiometry practice problems MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Iron metal reacts with the oxygen gas in air to form iron(III)oxide (rust). What is the conversion factor you wo...
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
Practice problems for thermodynamics 1) The dissociation of acetic acid has an equilibrium constant of 1.75 10-5 at 25C. What is the standard free energy change for this process at 25 C? 2) The standard free energy change for the dissociation of ...
UCLA >> CHEM >> 89 (Fall, 2008)
Gases 2 Practice Problems MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) According to the kinetic-molecular theory of gases: A) gaseous particles are in constant, nonlinear motion B) all coll...
UCLA >> CHEM >> 89 (Fall, 2008)
Matter, atoms and elements practice problems MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Oxygen gas is: A) a heterogeneous mixture C) a compound 2) Sulfuric acid dissolved in water is: A) ...
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
Review practice problems MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) All of the following are fundamental SI units except A) meter B) kilogram C) liter D) second E) kelvin 2) 1) 2) The pr...
UCLA >> CHEM >> 89 (Fall, 2008)
Chemistry12,Sections1249/1250 GeneralChemistryIIFall2008 OfficeHours:N/A Meetingtimesandlocations: 1.RequiredMaterials: Instructors:Dr.PeterDoucette Dr.WeniseWong Lectures: 1349Lab: 1350Lab: WF T Th 8:0010:30 7:0011:00 ...
UCLA >> CHEM >> 89 (Fall, 2008)
Additional Practice Problems 2 1) How many millimoles of carbon dioxide will be produced if 109.3 mg of 2,2-dimethyl propane is burned completely in excess oxygen? 1) 2) How many millimoles of carbon dioxide will be produced if 109.3 mg of 2,2-dim...
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
PIN 417 683 907 1173 1355 1399 1848 1977 2926 3394 3591 3606 3755 3788 3833 4497 4526 4680 4907 5314 5466 5491 6082 6550 6681 6879 7415 7526 8692 9020 9408 9422 9669 9783 HW1 HW2 HW4 HW5 HW6 HW7 HW8 HW ExpA Exp2 Exp4 Exp5 Exp14 Exp1 HLa...
UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
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UCLA >> CHEM >> 89 (Fall, 2008)
Formula mass, empirical and molecular formula practice problems MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) A 2.000 g sample of water contains 11.19% H by mass and 88.81% O by mass. What %...
UCLA >> CHEM >> 89 (Fall, 2008)
Practice problems for acids and bases 3 1) If one mole of Ba(OH)2 is added to enough water to make 10 liters of solution, the pH of the resulting solution is: A) 13.3 B) 0.7 C) 12.5 D) 1.0 E) 13.0 2) What is the pH of a 0.250 M solution of formic ac...
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