Midterm 1 Key - Manashi Chatterjee Ph D Chem 30A Winter...

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Unformatted text preview: Manashi Chatterjee, Ph. D. Chem. 30A - Winter 2008 LaSt First Name Name K E Y Student ID Number : l Signature I Name of your TA: Bree / Eric (Please Circle) Discussion Section - Day : Total: / 100 Chem 30 A Winter 2008 Midterm # 1 I ' ' ‘ : “i l (50mins) H’fih‘f“ S C W Wednesday A V3 : 5 ‘1 January 30, 2008 ‘ DO NOT OPEN THIS EXAM UNTIL INSTRUCTED TO DO SO Manashi Chatterjee, PhD. Chem. 3 0A — Winter 2008 1. [3 POINTS] What is the name of the compound shown below? a) bicyclo[3.2. l]octane V . b) bicyclo[5.4.3]octane c) bicyclo[3.2.l]heptane ' d) bicyclo[2.2.l]octane 2. [3 POINTS] Which of the following is the most stable conformation of trans-l-ethyl-3- methylcyclohexane? “79.95 a 5 +ra as M ()6 WV M I 11 111 IV W a” “a?” (c) III (ELI—Y 3. [3 POINTS] Consider the three conformers and answer the questions below. CH CH3 CH3 0 H 3 H H 0sz H H 2 5 H CCH H C(CH3)3 H C(CH3)3 ( 3>3 H Csz H 11 Ill \ I . VX- b) The conformation with the most torsional strain is: Answer is \ a) The conformation with least torsional strain is: Answer is -w/ c) If the tert-butyl group is replaced by a—CN (cyanide) group the torsional strain of the new molecule: increases ordkecreases-or remains unchanged. Answer is ACTIVATE/‘3‘” :3 Manashi Chatterjee, PhD. Chem. 30A — Winter 2008 4. (12 POINTS) For each of the pairs shown, enter the letter of the term that best describes the relationship between them as: A. Equivalent representations of the same compound B. Conformers C. Constitutional isomers D. Cis and trans isomers E. None from A—D As answers, place the letter of the terms in the square boxes to the right of each pair. n05: ax (:th r -»~}7'\ r pl Manashi Chatterjee, PhD. Chem. 30A - Winter 2008 5. [18 POINTS] Complete the Lewis dot structure of each of the molecule shown below. Draw two resonance forms for each of the molecules. Draw pr0per curved arrows to show movement of electrons. (if’l‘f‘mi‘) ‘- Lg‘ugx’) ("\CA th'uchlfl w wl Manashz' Chatterjee, PhD. Chem. 30A - Winter 2008 6. [8 POINTS] Label all of the functional groups present in compound shown below (circle the functional group on the structure and write the name next to it). _ V //’/ H“? I (“A (\Ci /' 6H 7. [9 points] Draw the complete orbital picture diagram of an ester HCOOCH3 showing how the orbital of each atom overlap to form bonds in the molecule. Label the bond anaglesbhxbrid orbitals , sigma and pi bonds and indicate how they are formed. 3 Oxygen SP 393:8 ~ 00 do“ matched Manashz' Chatterjee, PhD. Chem. 30A - Winter 2008 7. [6 + 10 POINTS] a) Circle the two structures (among I - IV) that represent a conformation of 3,3- dimethylpentane Viewing along any C-C bond. H H H \W/ 11 , ,. H H 619* i) H H H HSC CH3 0 3 C3sz CH3 CHzCHs H30 (3H3 H CH3 H H 5 HI H30 H CH Q] 2 CH3 Hsc/ b) Draw the Newman projections below to show the most stable and the least stable conformations of 3,3-dimethy1pentane Viewing along C2-C3 bond. ext 5 Most stable Manashz' Chatterjee, PhD. Chem. 30A - Winter 2008 8. [12 POINTS] 21) Draw the planer hexagonal representation of the molecule shown below. Draw in the substituent and all hydrogen’s on the chair and the alternate chair conformers of molecule and predict which conformer is lower in energy. planer hexagonal representation Note: A G0 (Axial to Equitorial) for monosubstituted cyclohexane at 25°C C1 = 2.2 kJ/mol; NH2 = 5.9 kJ/mol; CH3 = 7.28 kJ/mol Conformer l 5 has the lowest energy because DQCUAg Manashi Chatterjee, PhD. Chem. 30A - Winter 2008 9. [6 POINTS] a) In the molecules shown below label each Chiral carbon with * and write the total number of chiral carbons in the box below the compound. Noe H “k H H H N’ H C H ‘k 2 H *2 5 CH a? Br 3 CH3 E 771W :1?" Lil axfix 5 10. [4 points] Circle the cycloalkane that has the highest angle strain? Explain why (10 words or less) a) cyclohexane c) cyclobutane Explanation: ."' 11. [6 POINTS] Name the compounds according to the IUPAC rules. ...
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