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CHEM 2311HOUR EXAM INAME ___________________30 SEPTEMBER 2010100 POINTS TOTAL1. What is the correct name of the following compound according to IUPAC rules? (7 points)2. Dipole moments of alkyl chlorides and alkyl alcohols are strikingly similar yet alcoholsboil much higher than the corresponding chlorides. Briefly explain the observed difference. (5 points)3. Supply the formal charges for the four atoms in the following compound (4 points)1HC NO. .. .. .. .24. Indicate which of the following is the stronger acid and briefly explain why. To say "because as you go ________ the periodic table, acidity __________" is not sufficient. (6 points)(a) HF and H3COH(b) H2Se and H2Te(c) 5. How many sp2 hybridized carbon atoms are present in the following molecule? (5 points)36. How many 1o (primary) carbon atoms are present in the molecule in Question 13 above? (5 points)47. Is propene considered a Lewis Acid or a Lewis Base? Explain your logic. (5 points) 8. Give a proper name for the following compound (can choose IUPAC, trivial or a combination). (8 points)9. Draw a Potential Energy Diagram for an exergonic reaction that is very fast. (4 points)R x n C o o r d i n a t eE10. Draw the most stable chair conformer of trans-3-t-butyl-1-methylcyclohexane. (5 points)511. Provide the proper IUPAC name for the following compound. (9 points)B r12. Looking down the C3-C4 bond, draw the lowest energy conformer (using a Newman Projection) for the compound shown below. (6 points)C l13. Provide the proper IUPAC name for the following compound and draw the other chair conformer. (4 points)B r 6714. What two atomic orbitals are overlapping to form the -bond in ethyne (HC CH). (3 points)(a) (2sp2, 2sp2)(b) (2sp3, 2sp3)(c) (2sp, 2sp)(d) (2p, 2p)(e) (2sp, 1sp)15. Which statements is/are true? (3 points)(a) The major reason why the staggered conformer is preferred is due to steric strain.(b) The major reason why the staggered conformer is preferred is due to -bonding orbital donation into the * orbital.(c) The eclipsed conformer is preferred.(d) The gauche term is used when the two substituents are as far apart as possible.16. In which molecule is the central atom sp3 hybridized? (3 points)( a )( b )( c )( d ) S o m e o f t h e a b o v e( e ) A l l o f t h e a b o v eC H4N H3. .. .H2O. .( f ) N o n e o f t h e a b o v e17. Which molecule would you expect to have no dipole moment? (3 points)( a )( b )( c )( d )( e ) C H2F2C H F3N F3. .CCFFHHCCFHFH18. Which is not an intermolecular force? (3 points)(a) Van de Waals (d) Resonance(b) Dipole-Dipole (e) Hydrogen bonding(c) Induced Dipole19. Which of the following is a true statement? (3 points)(a) The stronger the acid, the larger its pKa.(b) The conjugate base of a strong acid is a strong base.(c) Acid-base reactions always favor the formation of the stronger acid and the stronger base.(d) Strong acids can have negative pKas.(e) Hydrogen need not be present in the molecular formula of a Bronsted-Lowry acid.820. Which of the following are Nucleophiles? (3 points)( a )( b )( c )( d ) A l l o f t h e a b o v e( e ) N o n e o f t h e a b o v eZ nH3C O HH2N921. As a 2311 student – you were shocked to learn that the most stable conformer of CH2FCH2CH2+ looking down the C1-C2 bond was when the F and the CH2+ groups were gauche to one another. Provide a brief rationale why the gauche conformer was more stable than the other possible conformers. (6 points)100 POINTS TOTAL SCORE


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NU CHEM 2311 - Exam 1

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