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 will not 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 320 328 M Exam 1 Question 1 2 3 4 5 Section II Value 18 18 20 10 24 90 Section I Raw Total 60 150 Grade Score UTID September 2013 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 4pts ea 60 pts this section CH320 328M Exam 1 1 Which of the following substituents has the highest priority according to the Cahn Ingold Prelog system used in assigning R and S configurations a NHCH3 b NH2 c CH2NH2 d CH2NHCH3 2 Which of the following statements is not true regarding pairs of enantiomers a They have identical melting points b They react at identical rates with chiral reagents c They rotate plane polarized light in opposite directions d They have identical boiling points 3 Which of the following elements has the highest electronegativity a N b C c O d S 4 Which of the following cycloalkanes has the least ring strain a cyclopropane b cyclopentane c cyclohexane d cycloheptane 5 Which of the following have the S configuration a only 1 b only 2 c only 1 and 2 d 1 2 and 3 1 UTID ID D 6 Which of the following shows curved arrows that correctly accounts for the differences between the two structures a 1 b 2 c 3 d 4 7 Which of the following is a tertiary 3 alcohol a 1 b 2 c 3 d 4 8 Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups a cis 1 3 dimethylcyclohexane b cis 1 4 dimethylcyclohexane c trans 1 3 dimethylcyclohexane d cis 1 2 dimethylcyclohexane 9 Which of the following compounds is a carboxylic ester a CH3CH2OCH3 b CH3CH2COOCH3 c CH3CH2COOH d CH3CH2COCH3 2 UTID ID D 10 Which of the following resonance structures is the least important contributor to the resonance hybrid of the acetate anion CH 3COO a 1 b 2 c 3 d 4 11 Which of the following Newman projections represents meso 2 3 dibromobutane a 1 b 2 c 3 d 4 12 What is the name of the linear hydrocarbon with the molecular formula C 7H16 a hexane b heptane c decane d undecane 13 Which of the following conformations is least stable a 4 b 3 c 1 2 3 d 1 2 3 UTID ID D 14 Which of the following drawings represent the boat conformation of cyclohexane a 1 b 2 c 3 d 4 15 Complete the structure What are the other two groups for this compound to be S 2 butanol a group 1 CH2CH3 group 2 OH b group 1 OH group 2 CH2CH3 group 2 OH d group 1 CH2CH3 group 2 OCH3 4 c group 1 CH3 ID D CH320 328M Exam 1 Answer Section MULTIPLE CHOICE 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS ANS A B C C C C C A B C C B A C B PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS PTS 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 1 UTEID KEY CH 310 318 M EXAM 1 PART 2 Free Style Answer Format 75 pts in this section 1 In the boxes give the IUPAC name for the following hydrocarbons 18 pts methylcyclohexane cis 1 2 dimethylcyclohexane 5 1 3 dimethylcyclopentane UTEID KEY CH 310 318 M EXAM 1 2 For each of the following IUPAC names draw the line angle structure 18 pts 1 2 dimethylcyclopentane CH3 1 ethyl 2 methylcyclopentane CH2CH3 1 1 dimethylcyclohexane CH3 CH3 CH3 CH3 cis 1 2 dimethylcyclopentane 3 ethylpentane 2 methylpentane CH3 CH3 CH3 CH3 6 UTEID KEY CH 310 318 M EXAM 1 3 Newman Projections Draw the line angle structure in the middle box and give the IUPAC name in the box on the right 2 pts box 7 UTEID KEY CH 310 318 M EXAM 1 4 Configurational isomers Assign the follow chiral centers as R or S Show your assignment logic by drawing the groups around a circle giving priority 10 pts Cl Cl H CH3 HO HO CH3 S Chiral center is OH HO H CH2CH3 H3C H 3C Cl H3C CH2CH3 R Chiral center is Cl H CH2CH2CH3 OH R center is CH2CH2CHChiral 3 H 3C H OH H3C Br H CH2CH3 R Chiral center is Br R Chiral center is H3C CH2CH2CH3 8 UTEID KEY CH 310 318 M EXAM 1 5 Conformations in cyclic systems Draw a chair conformation of each compound in the first box and in the second box flip the ring and draw the second chair conformation a Label the methyl groups axial a or equatorial eq b Indicate which one is the most stable or if they are equal 24 pts END OF EXAM 9