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Give the IUPAC name for the following compound

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					                                                          CH221 ORGANIC CHEMISTRY I
                                                             QUIZ 1      2 MARCH 2009
                                                              Time allowed: 50 minutes
                                              Attempt all 40 questions on the grid answer sheet provided

                                                                             7. Which of the following species has (have) a trigonal planar structure
1. Which of the following is (are) a Lewis structure(s) for the anion        with 120 bond angles around the labeled carbon atom?
    (CH2NO2)-? Assume the atoms are arranged as drawn.E                      D




2 Convert the following compound from a condensed formula to a
    skeletal formula. D
    CH3CH2C(CH3)2CH2CH(CH2CH3)CH2CH(CH3)2
                                                                             8. Of the molecules listed, which does not have a dipole moment?
                                                                                  D
                                                                                 A. HCl
                                                                                 B. NCl3
                                                                                 C. CO
                                                                                 D. BF3
                                                                                 E. All molecules have a dipole moment.

                                                                             9. From the list below, pick the one species that cannot act as both a
3. How are the molecules in the following pair related?                           Bronsted-Lowry acid and base.
     B                                                                             D
                                                                                  A. HCO3-
                                                                                  B. HSO4-
                                                                                  C. H2PO4-
     A. They are isomers.                                                         D. OH-
     B. They are resonance structures.                                            E. HPO42-
     C. Neither of the choices is correct.
                                                                               10. Rank the acidity of the labeled protons in the following molecule
4. Indicate the hybridization at the carbon ion in each compound below.                           from lowest to highest acidity.
     D                                                                                                     Hc > Ha > Hb




     A. a - sp2; b - sp2   B. a - sp2; b - sp3                               11. Which of the following compounds is the strongest Bronsted Lowry
     C. a - sp3; b - sp3   D. a - sp3; b - sp2                                    acid?
     E. None of the choices are correct.                                           B
                                                                                  A. CH3CH2OH
5. Which of the labeled carbon atoms is (are) sp2 hybridized?                     B. ClCH2OH
  D                                                                               C. CH3OCH2F
                                                                                  D. ClCH2NH2
                                                                                  E. CH3CH3

                                                                             12. Which of the following species is the strongest base?
                                                                                  A
                                                                                  A. NH2-
                                                                                  B. OH-
 6. Which of the following species contains a carbon atom with a +1               C. Cl-
  formal charge? (All nonbonded electron pairs have been drawn in.)               D. NH3
  A                                                                               E. I-

                                                                             13. Which of the following statements is true?
                                                                                  C
                                                                                  A. CH3CH3 can be a Lewis base.
                                                                                  B. BBr3 can be a Bronsted-Lowry acid.
                                                                                  C. CH3Cl can be a Lewis base.
                                                                                  D. CH3CH3 can be a Lewis base, and BBr3 can be a Bronsted-
                                                                                      Lowry acid.
                                                                                  E. CH3CH3 can be a Lewis base, BBr3 can be a Bronsted-Lowry
                                                                                      acid, and CH3Cl can be a Lewis base.

                                                                                                                                               1
14. What is the nucleophilic site in each of the following molecules? C   21. A thiol should have properties most similar to A

                                                                               A.   an alcohol.
                                                                               B.   an amine.
                                                                               C.   an ether.
     A.   A: hydrogen; B: nitrogen; C:  electrons in bond                     D.   a sulfide.
     B.   A: oxygen; B: nitrogen; C: carbon                                    E.   an alkyl halide.
     C.   A: oxygen; B: nitrogen; C:  electrons in bond
     D.   A: oxygen; B: carbon; C:  electrons in bond                    22. Hydrogen bonding E
     E.   A: carbon; B: nitrogen; C: hydrogen
                                                                               A. requires at least one lone pair of electrons.
15. Estimate the pKa of the hydrogen to the nearest multiple of 5. D           B. is a common intermolecular bonding force in alkanes.
                                                                               C. can occur between a compound and water even if the
                                                                                  compound cannot hydrogen bond with itself.
                                                                               D. is the weakest of the intermolecular forces.
                                                                               E. requires at least one lone pair of electrons and can occur
     A.   10                                                                      between a compound and water even if the compound cannot
     B.   20                                                                      hydrogen bond with itself.
     C.   30
     D.   40                                                              23. Polarizability of molecules such as Br2 leads to E
     E.   50
                                                                               A.   an inability to interact with polar or non-polar solvents.
16. Which is the strongest base? B                                             B.   an induced dipole moment.
                                                                               C.   a molecule that can act as a nucleophile or an electrophile.
     A.   NH3                                                                  D.   an inert molecule.
     B.   NH2-                                                                 E.   an induced dipole moment and a molecule that can act as a
     C.   OH-                                                                       nucleophile or an electrophile.
     D.   H-
                                                                          24. The compound shown below is penicillin G. This was a "wonder"
17. Which of the following compounds has the lowest boiling point? E      drug for killing bacterial infections after World War II. Identify the
                                                                          functional groups a, b, and c listed in that order.
     A.   CH3CH2CH2CH2OH                                                    A : Phenyl, Benzyl or Arene B: Carbonyl or amide C: Carboxylic acid
     B.   CH3CH2OCH2CH3
     C.   CH3OCH(CH3)2
     D.   CH3CH2CH2CH2CH3
     E.   CH3CH2CH(CH3)2

18. Which of the following compounds has the highest boiling point?E


                                                                          25. From the list below, which compound would you predict to have the
                                                                               lowest boiling point? A

                                                                               A. CH4
                                                                               B. SiH4
                                                                               C. AsH4
19. Which of the following compounds is (are) the most water soluble? A        D. PH3
                                                                               E. NH3
     A.   CH3CH2CH2OH                                                     26. What is the IUPAC name for the following compound?
     B.   CH3CH2OCH3                                                       7,7-diethyl -2,3,7-dimethyl-5-isopropyl decane
     C.   CH3CH2CH2Cl
     D.   Both (CH3CH2CH2OH) and (CH3CH2OCH3) are H2O soluble.
     E.   Compounds (CH3CH2CH2OH), (CH3CH2OCH3), and
          (CH3CH2CH2Cl) are all H2O soluble.

20. Which of the following molecules can hydrogen bond to another
     molecule like itself? D                                              27. Give the IUPAC name for the following compound.
                                                                           4-tert-butyl-2,5-dimethylheptane
     A.   CH3CH2NH2
     B.   CH3COOH
     C.   CH3OCH2CH3
     D.   (CH3CH2NH2) and (CH3COOH) can hydrogen bond.
     E.   (CH3CH2NH2), (CH3COOH), and (CH3OCH2CH3) can all
          hydrogen bond.


                                                                                                                                                   2
28. Give the IUPAC name for the following compound.                      34. Which of the following statements is (are) true about the following
 5-sec-butyl-7,7-diethyl-2,3-dimethyldecane                                   compound? E




29. Draw the ring-flipped conformer of this compound?


               CH2CH3
                                                                                   A.   Ca and Cd are 1 carbons.
      H3 C
                                                                                   B.   Cb and Cc are 3 carbons.
H3CH2C
                                                                                   C.   Ce and Ca are 2 carbons.
                                                                                   D.   (Ca and Cd are 1 carbons) and (Cb and Cc are 3 carbons).
30. Draw the most stable conformer of 1, 3-dimethylcyclohexane.                    E.   (Cb and Cc are 3 carbons) and (Ce and Ca are 2 carbons).


                                                                         35. Which of the following Newman Projections represents the most
                                                                         stable conformation of 2,3-dimethylbutane? C
31. Given the three Newman projections drawn below, rank them in order
of increasing stability. B<C<A




                                                                         36. Which of the following curved arrows account for the differences
                                                                         between the two structures? 3
                                                                                    O                O

                                                                         1          C                C
                                                                             H2C        H     H 2C       H

                                                                                    O                O
32. Assuming that the size of substituents is H<CH3<I, which of the
                                                                         2          C
following conformations is the most stable? C                                H2C        H     H 2C
                                                                                                     C
                                                                                                         H

                                                                                    O                O

                                                                         3          C                C
                                                                             H2C        H     H 2C       H

                                                                                    O                O

                                                                         4          C                C
                                                                             H2C        H     H 2C       H



                                                                         37. How many constitutional isomers are there with the molecular
                                                                         formula C6H14? C
                                                                         a. 3             b. 4                 c. 5                d. 8

                                                                         38. Which of the following compounds can adopt a chair conformation
33. How are the molecules below related to each other? C                 in which there are no axial methyl groups? C or D
                                                                         a. 1,1-dimethylcyclohexane             b. cis-1,2-dimethylcyclohexane
                                                                         c. trans-1,2-dimethylcyclohexane       d. cis-1,3-dimethylcyclohexane

                                                                         39. Which of the following cycloalkanes has the smallest heat of
                                                                         combustion per carbon atom? C
                                                                         a. cyclopropane      b. cyclopentane
                                                                         c. cyclohexane       d. cycloheptane
     A.   They are constitutional isomers.
     B.   They are identical.                                            40. Which of the following substituted cyclohexanes has the most
     C.   They are resonance structures.                                 negative value of ΔG° for ring flipping from the conformation in which
     D.   They are not isomers; they are different compounds.            the substituent is axial to the one where it is equatorial? D
     E.   They are stereoisomers.                                        a. fluorocyclohexane
                                                                         b. methylcyclohexane
                                                                         c. ethylcyclohexane
                                                                         d. tert-butylcyclohexane


                                                                                                                                                     3
                                  CH221 QUIZ 1      ANSWER GRID

     Write in each box the answer you think corresponds to the correct answer to that question.


Name……………………………………………..                                    Student Number…………………….……………


1                   2                    3                     4                    5

       E                   D                     B                    D                      D
6                   7                    8                     9                    10

       A                   D                     D                    D              Hc>Ha>Hb

11                  12                   13                    14                   15

       B                   A                     C                    C                      D
16                  17                   18                    19                   20

       B                   E                     E                    A                      D
21                  22                   23                    24
                                                               A : Phenyl or Benzyl B: Carbonyl or amide
       A                   E                     E                         C: Carboxylic acid

25                  26                   27                    28
                    7,7-diethyl-5-         4-tert-butyl-2,5-
       A            isopropyl-2,3-        dimethylheptane      5-sec-butyl-7,7-diethyl-2,3-dimethyldecan
                    dimethyldecane
                                         30                                         31

                                                                                    B<C<A
29

32                  33                   34                    35                   36

C                   C                    E                     C                    3
37                  38                   39                    40

C                   C or D               C                     D                         Total score




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