CH151 Exam1KEYF06

CH151 Exam1KEYF06 - Organic Chemistry EXAM I CHEM 15 IL October 4 2006 NAME(Last First MI 5464 Write the first letter of your last name in the box

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Unformatted text preview: Organic Chemistry EXAM I CHEM 15 IL October 4, 2006 NAME (Last, First, MI.) 5464 Write the first letter of your last name in the box. Instructions _ - Please fill in your name in the space above and on the next page. Print the initial of your last name in the box above. _ _ g _ - _ Sign your name under the Community Standard Acknowledgement. You may use pencil. ' ' - I Answer questions in the spaces provided. If you need eXtra space please write on the back of the page and clearly indicate that you have done so. 'If you do not know. the structure of a molecule given by its name you can “buy” it from the TA for 1 point (each). ' ' _ GOOD LUCK!!! ' I: D'EJEJEJEJEJ - 1) a) '(6 points) Provide the complete IUPAC name for the compound shown below. CHsCH20H2 H \C=C/ CH CH H/ \l?’ 2 3 9‘ H30 H (92/415)- 3 - amlodwgfme b) (6 points) Draw the skeletal line structure for 4—terE-butyl-3-methylheptane. 2) - . . a) (5 points) Label the nucleophilie atom (NUC) and the electrophilic atom (E) for the acid base reaction shown below. b) (8 points) Predict the products of the following acid base reacfion._ c) (5 points) Show the electron movement (mechanism) that leads to the expected products. Be sure to include formal charges where appropriate. d) (8 points) Predict whether the equilibrium lies to the RIGHT or LEFT and . BRIEFLY EXPLAIN your reasoning. " ' eua/@\C°F§)9 - I I I '. 93$)“ sCHchZCHzcl-la + H-N)? === 4 In" T __ T . E 3) (24 points) a) (6 points) Circle the most acidic proton on lactic acid. b) (6 points) Circle the base that would react with H20 to give the highest concentration of H0" at equilibrium. re #36 a“? c) (6 points) Circle the molecule with the smallest pKa: 03w . co ‘ I d) (6 points) Based on the pKa values provided, circle the molecule you expect to be in highest concentration at equilibrium? 4) a) (10 points) Draw the Newman Projections of 2-methylhexane citing down the C3-C4 bond depicting the highest and lowest energy conformational isomers. Aw 3 2-methylhexane H fir HM“ K H:- C6) Cdtpjeél @ 0o?“ HIGHEST ENERGY LOWEST ENERGY b) (8 ts) Circle kind of strain that is present in the highest energy isomer: ‘-' f3 1 torsional strain angle strain lack of chocolate strain c) (15 points) i) Show both chair conformations of cis—1-isopropyl-Z-methylcyclohexane. Full credit for those structures that clearly show axial and equatorial bonds on carbons l and 2. '- - ' ii) Circle the conformatia you aspect to be present in highest concentration at equilibrium. ' ‘ 5) (17 points) a) Predict the MAJOR product of the BOTH of the following reactions. PMQUC'Z .7559"; 6400‘ 6) a) (8 points) Provide the major product for the 'on below. 3 excess H2(9) ’L-E PdIC h (ix N \ | I i >1 913% I limonene to {TB 2: P A {— Crag! b) (5 points) Which of the following statements are true? Equal molar quantities of the 112(3) and PdlC are required. he Pd/C increases the rate of the reactio Other catalysts, like H2504 or I-INO3 could be substituted for the PdfC to give the same product. c) (5 points) Circle the graph below that best demonstrates why raising the temperature of a r ' often leads to an increase in the reaction rate. T] < T2 _ Kinetic Energy . 7) (20 points) Reaction a proceeds significantly faster than reaction b. ' a) Below is an energy diagram for reaction a. Complete the energy diagram for reaction b. Pay close attention to the relative energies of the intermediates and the transition states leading to the intermediates. Clearly label the rate determining step (RDS), the transition state (:t) and the activation energy of the RDS (AG‘). b) Use the diagrams to explain the observed relative reactivity (invoke Hammond’s postulate). H c H B’ H c H Br 3 H + H—Br —- H30-¢-CH3 3 H + n-3, _. “30-54% H36 H CH3 H H ,1. Reaction 3 Rea 'on b {n+6 meatak 4 $35 . Ts. 4+ - L‘ka energy WA“:- free if myopafimflld‘ba/fl en wt; in Mam we mfl mead am. @am' I I IHC-I 2°:‘Carlmcaiééw :21-_/2?ac;£,i£_, II _ SS @143 i low in m yith .‘Fu5_»i.C$eqéM33_. L - .- r «7 "Ty-$133 amass ' ' . . I lea-IS 46 a. f'eaofi'fyp,@v 2 -_ . . ' I "Slit-H6 are _ ...
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This note was uploaded on 05/13/2010 for the course CHEM 151L taught by Professor Roy,christopher during the Summer '08 term at Duke.

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CH151 Exam1KEYF06 - Organic Chemistry EXAM I CHEM 15 IL October 4 2006 NAME(Last First MI 5464 Write the first letter of your last name in the box

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