LAST NAME FIRST NAME UTEID COVER PAGE Instructions This exam will be closed book No notes books calculators or molecular models will be allowed The exam will be comprised of two distinct parts Part I will consist of a series of multiple choice questions Your answers to these questions must be submitted on a Scantron bubble sheet The answer sheet will be provided for you but you will need your own 2 pencil s Only answers marked on the bubble sheet will be graded Answers to Part I questions marked on the exam itself cannot not be graded No re grades will be possible on Part I of the exam Part II consists of questions for which you will need to write out your answers using structures and or words This part of the exam will be hand graded Answers for the Part II questions that are written in pencil will not be eligible for re grades Answers written in pencil with ink overlay will not be eligible for re grades If you use a pen to answer the Part II questions only blue or black ink is acceptable Answers written in red ink cannot be graded 1 You must have your valid UT ID card or other government issued ID with you You will need to show it to the proctors when you turn in your exam 2 Chapter 4 of the University s General Information catalog outlines this university s policies regarding exams as well as other quizzes administered during the semester Specifically students are expected to remain in the exam room until a test is completed These policies will be strictly enforced with no exceptions You may not leave the room for any reason until you are ready to turn in your exam If you wish to leave the room you will need to turn in your exam to the proctors and you will not be allowed to return Please plan accordingly by using the rest room before the exam starts CH 310 318 M Exam 1 Question 1 2 3 4 5 6 Section II Value 16 13 12 10 14 10 75 Section I Raw Total 75 150 Grade Score UTID September 2010 CH310 318M Exam I v2 0 Objective Test Section Identify the choice that best completes the statement or answers the question There is only one correct answer please carefully bubble your choice on the scantron sheet 3pts ea 75 pts this section 1 Which of the following structures have a plane of symmetry a b c d only 1 and 2 only 2 and 4 only 3 and 4 1 2 3 and 4 2 Which of the following Newman projections represents meso 2 3 dibromobutane a b c d 1 2 3 4 3 What is the IUPAC name of the following compound a b c d trans 1 tert butyl 2 methylcyclopentane cis 1 tert butyl 2 methylcyclopentane trans 1 isopropyl 4 methylcyclopentane cis 1 isopropyl 2 methylcyclopentane 1 4 Which of the following Newman projections represents the most stable conformation of 2 3 dimethylbutane a b c d 1 2 3 4 5 Which of the following structures represent the same stereoisomer a b c d only 1 and 2 only 1 and 3 only 2 and 3 1 2 and 3 6 What is the IUPAC name of the following compound a b c d isooctane 3 propylpentane 3 ethylhexane 1 1 diethylpropane 2 7 Which of the following compounds is are chiral a b c d only 1 only 1 and 2 only 2 and 3 1 2 and 3 8 How many hydrogen atoms are there in dodecane the linear hydrocarbon with twelve carbon atoms a 20 b 26 c 12 d 24 9 Which of the following is the definition of chirality a The non superposability of an object on its mirror image b A molecule with a mirror image c A molecule that has a carbon atom with four different substituents d The superposability of an object on its mirror image 10 How many hydrogen atoms are there in nonane the linear hydrocarbon with nine carbon atoms a 18 b 22 c 20 d 16 11 What is the IUPAC name of the following compound a b c d 2 isopropyl 5 methylpentane 5 isopropyl 2 methylpentane 2 3 5 trimethylhexane 1 2 diisopropylpropane 12 Which of the following compounds has 1 2 3 and 4 carbon atoms a 2 2 3 trimethylhexane b hexane c 2 2 dimethylhexane d 2 methylhexane 3 13 Which of the following cycloalkanes has the most ring strain a cyclobutane b cyclohexane c cyclopropane d cyclopentane 14 Which of the following statements is true a Superposable structural isomers are enantiomers b All molecules that have stereocenter centers are chiral c Isomers that are not superposable on their mirror images are enantiomers d All mirror images are enantiomers 15 What is the approximate C C C bond angle in propane a 120 b 180 c 90 d 109 16 Which of the following anions is the strongest base a NH2 b Cl c HO d CH3COO 17 Which of the following statements regarding optical rotation is not true a All R enantiomers are dextrorotatory b All enantiomers rotate plane polarized light in a counterclockwise direction c All enantiomers are dextrorotatory d All and enantiomers rotate plane polarized light in opposite directions 18 Which of the following alkanes has the highest boiling point a pentane b propane c hexane d butane 19 Which of the following is the definition of a meso compound a A molecule with stereocenter centers which is not chiral b A chiral compound with more than one stereocenter center c A diastereomer with no stereocenter centers d A molecule with stereocenter centers which is chiral 20 What is the approximate dihedral angle between the two chlorine atoms in the diequatorial conformation of trans 1 2 dichlorocyclohexane a 0 b 180 c 60 d 120 4 21 Which of the following is the correct order of decreasing basicity stronger base weaker base a CH3COONa NaOH NaOMe NaNMe2 b MeNH2 NH3 MeOH CH4 c NH3 Me3N H2O MeOH d NH3 MeNH2 H2O HF 22 Which of the following have the R configuration a b c d only 1 only 2 only 1 and 2 1 2 and 3 23 Which of the following is the strongest acid a CH4 b HC CH c CH2 CH2 d CH3CH3 24 Which of the following is the definition of a pair of diastereomers a A pair of stereoisomers that are not mirror images of one another b A pair of structures that are superposable mirror images of one another c A pair of stereoisomers that are non superposable mirror images of one another d A pair of stereoisomers that have equal specific rotations 25 What is the correct assignment of common names for the following molecules a b c d i butane ii isobutane iii isopentane i butane ii neopentane iii isopentane i butane ii isobutane iii neopentane i neobutane ii isobutane iii pentane 5 ID A CH310 318M Exam I Answer Section v2 0 MULTIPLE CHOICE 1 2 3 4 …