Practice Exam II - CHM 238 Organic Chemistry I Practice...

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CHM 238 Organic Chemistry I Practice Exam II [319 points total] [( 319 points total - _____ points missed) / (319 points total)] * 100 = grade NAME __________________ For each multiple choice question below, write the letter of the correct choice in the blank provided. (2pts each) Circling the answer will not be accepted and multiple choices will be considered wrong. 1. ____What is the IUPAC name of the following compound? a. 1-Isopropyl-2,5-dimethylcyclohexane b. 2-Isopropyl-1,4-dimethylcyclohexane c. 1,4-Dimethyl-2-isopropylcyclohexane d. 1,4-Dimethyl-3-isopropylcyclohexane 2. ____Which of the following is an acceptable IUPAC name? 3. ____What is the IUPAC name of the following compound? 4. ____How many constitutional and cis trans stereoisomers are there of cycloalkanes with the formula C 5 H 10? 1
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5. ____Which of the following pairs of structures are constitutional isomers of one another? a. 1 b. 2 c. 3 d. 4 6. ____Which of the following cycloalkanes has the least ring strain per carbon atom? 7. ____Which of the following compounds has all of the carbon atoms in a plane in its lowest-energy conformation? 1. Cyclopropane 2. Cyclobutane 3. Cyclopentane 4. Cyclohexane 8. ____What is the approximate C C C bond angle in cyclohexane? 9. ____Which one of the following structures represents a different compound from the other three? a. 1 b. 2 c. 3 d. 4 2
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10. ____Which of the following represents menthol in its most stable chair conformation? 11. ____What is the approximate dihedral angle between the two chlorine atoms in the diequatorial conformation of trans- 1,2-dichlorocyclohexane? 12. ____Which of the following structures represents trans- 1,2-dimethylcyclohexane? 13. ____Which of the following statements is not true regarding the conformation of cyclohexanes? a. Ring inversion of substituted cyclohexanes swaps the equatorial and axial positions of the substituents. b. Conformations of substituted cyclohexanes are stabilized by 1,3-diaxial steric interactions. c. The chair conformation of cyclohexane is more stable than the boat conformation. d. The relative amount of two conformations of substituted cyclohexanes can be determined from the difference in strain energy.
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