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CHM 201 E -- Examination I -- 27 Sep 1999

This examination comprises 33 questions.

01. In geometric shape, a methane molecule is:

02. The IUPAC name of isobutyl bromide is:03. Isopentane is an isomer of:04. Of the following, an incorrect IUPAC nameis:05. The pair of constitutional isomers among thefollowing is:06. The IUPAC name of 
                         CH3-CH2-CH2                                 |                             CH3-CH2
is:07. The IUPAC name of 
                                CH3-CH2                                     |                             CH3-CH2-C-CH3                                     |                                     CH2                                     |                                 CH3-CH-CH3
is: 08. The compound among the following that hasone or moretertiary hydrogens is: 09. Covalent bond formation between an ethylfree radical and atert-butyl free radical produces:10. The molecular formulaC8H16 cannot represent:11. A name that is not a correct IUPAC name forone of theisomers of C4H9Br is:12. The IUPAC name of
                                 CH2                                /  \                               CH2  CH-CH3                               |    |                               CH2  CH2                                \  /                                  C                                 / \                               CH3  CH3
is:USE THE FOLLOWING GRAPHIC FOR QUESTIONS 13 AND14

13. Which one of the curves represents a portion of the potentialenergy vs. bond rotation graph for rotation about the C1-C2 bondin 2-methylbutane, 

                   CH3-CH-CH2-CH3                       |                       CH3
:14. Which one of the curves represents a portionof the potential energy vs. bond rotation graph for rotationabout the C2-C3 bond in 2-methylbutane, 
                   CH3-CH-CH2-CH3                       |                       CH3
: 15. Adolph von Baeyer reasoned (incorrectly)that of all thecycloalkanes, cyclopentane should show the smallest ring-strainenergy because:16. In actual fact, of all the cycloalkanes it iscyclohexane that shows the smallest ring-strain energy. This isbecause:17. The cycloalkane ring with the largest amountof ring-strainis:Use the following in answering Questions 18-20
Q) cis-1,2-dimethylcyclohexane   R) trans-1,2-dimethylcyclohexaneS) 1,1-dimethylcyclohexane       T) chair cyclohexane                   U) boat cyclohexane
18. Configurational isomers:19. Conformational isomers:20. Constitutional isomers:21. A cycloalkane that can exist in aconformation containing twoaxial methyl groups [Please note; Four of the following arecyclohexanes, one is a cyclopropane.]:22. When the chair conformation oftrans-1,2-dimethylcyclohexaneundergoes a ring-flip, the product is:23. The total number of conformations in whichcis-1,4-dimethylcyclohexane can exist is:24. A common feature of decalin, camphor, andcholesterol is:25. The difference between the total amount ofenergy in theproducts of a reaction and the total amount of energy in itsreactants is:26. Given the following values for bonddissociation energies,
Bond      D (kJ/mol)H-H       436H-Cl      432Cl-Cl     243H2C=CH-H  444H2C=CH-Cl 368
the heat of the following reaction

H2C=CH2 + Cl2 -----> H2C=CH-Cl + H-Cl

is (ignoring the algebraic sign):

27. The bond dissociation energy ofH2 is 436 kJ/mol. We conclude that:28. A compound of molecular formula C10H14undergoes catalytichydrogenation but absorbs only two molar equivalents of hydrogen.How many rings does the compound have: 29. The degree of unsaturation in DDT,C14H9Cl5 is: 30. According to the Cahn-Ingold-Prelog sequencerules, the orderof priority for methyl, bromine, hydrogen, and iodinesubstituents from highest priority to lowest priority is:31. The E,Z-system is not applicable to:32. The alkene that releases the smallest amountof heat, per mole, when it is hydrogenated to an alkane is:33. Markovnikov's Rule concerns:
= THE END =
You now have the choice of: