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W07 midterm1 key

W07 midterm1 key - Dr Manashi Chatterjee Chem30A Winter...

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Unformatted text preview: Dr. Manashi Chatterjee Chem30A- Winter 2007 Last first - " El Student 1]) Number : “ Name of your TA: . (Please Circle) Greg / Paul _/ Erlc Total: / 100 Chem 30 A Winter 2007 Midterm # 1 (50mins) Wednesday January 31, 2007 Electronegativity values for some atoms (Pauling scale) DO NOT OPEN THIS EXAM UNTIL INSTRUCTED TO DO SO Dr. Manashz' Chatterjee Chem3 0A- Winter 2007 1. (15 POINTS) Complete the Lewis dot structure of each of the molecule shown below. Draw two resonance forms for each of the molecules. Draw proper curved arrows to show movement of electrons. lonerair as» Pyridiflcv is not delomflt'zccfi I'h +he ring Dr. Manashi Chatterjee Chem30A- Winter 2007 2. [3 POINTS] The anticipated hybridizations for the carbon-nitrogen-carbon in the order they appear in the given structure, are: <9 e H2C=N=CH2 Br (a) sz, spz, 8132 (b) Sp,sp, sp a (C) SP3, Sp, SP3 (60 sz, Sp, SP2 3. [3 POINTS] Aldosterone is one of many steroid hormones. Which of the given choices represents an accurate list of the functional group classes in aldostcrone molecule shown below? “0 CHon (a) two alcohols, three ketones, and an alkene (b) an ether, an alcohol, three ketones, and an alkene D (c) an alkyne, three aldehydes, two alcohols, and a ketone ((1) two ketones, an alkene, an aldehyde, and two alcohols 4. [3 POINTS]How many secondang class carbon atoms are present in the following structure: Cl cmcmficmcmh CH3 Dr. Manashz‘ Chatterjee ' » Chem30A- Winter 2007 5. [3 POINTS] Which of the following pairs of representations depict the interrelationships to be correctly called as contributing resonance structures of a same molecule? I H3C—§—CH3 ‘_—"' H_9—'CH2~CH3 H\ .. <9 I] /C=O <——> H—CEO H .. (9 G) In CHg—CHT—CH—CHz ‘——’ CHa‘—CH—CH:CH2 e .. ..__ .. 9 IV = N=c=o “"'—“* N=C‘9_‘ (a) II and III only (b) 11, HI and IV only (c) II and IV only (d) 111 and IV only 6. [3 POINTS] What will be the ranking order for the stabilities of the following three conformations, shown as Newman projections, of 2,2,3-trimethylpentane? CH3 H CH3CH3 CH3 C(CH3)3 CH3 C(CHah @ H H CH: H ”H fi‘°”°’° H H I 11 III (a) most stable H > III > I least stable (b) most stable 111 > 11 > I least stable (c) most stable I > 11 > III least stable (d) most stable II > I > III least stable 7. [3 POINTS] Which of these represents the best three—dimensional representation for ammonium chloride (NH4C1)? H 9 (fl l I].l ”\QSH Cal H ----- N—H H ---- N—CI H—-N—- N ”(IL ”(IL ll g H/ \H Cl (8) (b) (C) (d) Dr. Manashi Chatterjee Chem30A- Winter 2007 8. [3 POINTS] Which of the following three-dimensional representations are for the trans isomers of 1,2-dimethylcyclohexane? H CH3 H CH3 CH3 H fin”: $fl ELF" fl”. CH3 CH3 CH3 CH3 1 11 111 IV @11de (bum (c) I, H and IV (d) II and III 9. [3 POINTS] What name correctly corresponds to the condensed formula: (CH3)2CHC(CH3)3 (a) l-isopropyl-l,1,1-trimethylmethane (b) 1,1,2,2,2-pentamethylethane (c) 2-tert-butylpropane (d) 2,2,3-trimethylbutane 10. [3 POINTS] What molecular formula does the given skeletal structure of Vitamin C correspond to: HO HO HO OH Vitamin C (a) C5H606 (b) C61'1406 (c) C6H606 (d)C6H806 Dr. Manashi Chatterjee . Chem30A- Winter 2007 11. [13 POINTS] a. Draw the skeletal (line structure) structure for 2, 2-dimethy1butane. (2 POINTS) >29 3 b. Draw the Newman projection looking down the C3-C2, for any two staggered and one eclipsed conformational form that the molecule will pass through as a 360 ° rotation around the C3-C2 bond occurs. (9 POINTS) c. Comment on the stability of the staggered forms with a reason (within 10 -15 words). (2 POINTS) Dr. Manashi Chattery'ee Chem3 0A- Winter 2007 12. [16 POINTS] a) Provide the orbital hybridization for the atoms in bold in the molecule below. sp‘ b) Describe the correct overlap of atomic orbitals to form the bonds that are indicated by the arrows. (eg. sp3-sp3 overlap) 3 s 3-- S SP-SP 0" P P Cl / V\”/\ O H 6?2" 5?; SP "' .5 c) How many 1: bonds are present in the above molecule? Dr. Manashi Chatterjee Chem30A- Winter 2007 13. (12 POINTS) For each of the pairs shown, enter the letter of the term that best describes the relationship between them as: A. completely equivalent representations of the same substance B. Enantiomers C. Constitutional isomers D. Conforrners As answers, place the letter of the terms in the square boxes to the left of each pair. $H20H3 (szCHs 0 CH3 NOH c 11111 C'Iu ‘l H/ \ CH3 H3C/ \ H {I Q CH3 CH3 COOH COOH 0 K; 7 \ c ,,,,, c ::::: ’H 9H F/ \ F F/ \ F CHZOH F not drum] ”3 H ’ CH H3O 3 H CH3 a M w \ \\\\\ CH3 Br H H Br CH3 14. [9 POINTS] Draw structural formulae of a) one primary (1°) amine b) one secondary (2°) amine 0) one tertiary amine (3°) with molecular formula C4H11N. /‘\N/ 02 Secondary Tertiary Dr. Manashi Chatterjee Chem30A-Winter 2007 15. [8 points] Describe using Valence Bond Theory (V ET) the orbitals used in bonding and the bond angle (C-C-N) in H3CCN. Show the ground state electronic configuration, and hybridization of atomic orbitals of each atom involved. ...
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