LAST NAME FIRST NAME UTEID 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 N Exam I MWF 11 AM Question 1 2 3 4 5 6 Section II Value 15 16 12 12 10 10 75 Section I Raw Total 75 150 Grade Score UTID February 2011 CH310N Exam I Version 1 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 feature in the 1H NMR spectrum provides information about the electronic environment of the protons in a compound a splitting b chemical shift c integral d number of signals 2 What is the major organic product obtained from the following sequence of reactions a b c d 1 2 3 4 3 Which of the protons in the following molecule appear furthest downfield in the 1H NMR spectrum a b c d i ii iii iv 1 4 What is the major organic product obtained from the following sequence of reactions a b c d 2 methylbutane 3 methyl 2 butene 3 methyl 1 butanol 3 methyl 2 butanol 5 Which C8H10 compound gives the following 1H NMR spectrum a b c d 1 2 3 4 6 Which of the following laws relates the frequency of a stretching vibration to the masses and spring constant of a simple harmonic oscillator a Pan s law b Barrie s law c Peter s law d Hooke s law 2 7 What is the major organic product obtained from the following reaction a b c d 4 methyl 1 pentene 4 methyl 2 pentanol 2 methypentane E 4 methyl 2 pentene 8 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 9 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 3 10 Which of the following alcohols can be prepared from a Grignard reagent and ethylene oxide a b c d only 1 only 1 and 2 only 1 2 and 3 1 2 3 and 4 11 Which of the protons in the following molecule appear furthest downfield in the 1H NMR spectrum a b c d i ii iii iv 12 What is the hydrogen deficiency index for a compound with a molecular formula of C 10H16O2 a 1 b 2 c 3 d 4 13 Which feature in the 1H NMR spectrum provides information about the number of neighboring protons of each proton in the compound a integral b chemical shift c number of signals d multiplicity 4 14 Which C8H10 compound gives the following 1H NMR spectrum a b c d 1 2 3 4 15 Which combination s of alkyl bromide and carbonyl compound can be used to prepare the following product by reaction of the Wittig reagent derived from the alkyl bromide with the carbonyl compound a b c d only 1 and 2 only 2 and 4 only 2 and 3 only 1 2 and 3 5 16 What is required for a bond to give an infrared absorption a a change in reduced mass during vibration b a change in bond angle during vibration c a change in bond dipole during vibration d a change in bond length during vibration 17 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 18 Which feature in the 1H NMR spectrum provides information about the number of types of different protons in a compound a integral b number of signals c splitting d chemical shift 6 19 Which combination s of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound a b c d only 1 only 3 only 1 and 3 only 2 and 4 20 Which of the following functional groups is likely to be present in a molecule that has peaks in the infrared spectrum at 3200 3650 cm 1 strong but does not have peaks at 1630 1820 or 1000 1250 cm 1 a alcohol b aldehyde or ketone c ether d ester 21 What is the correct assignment of the names of the following aldehydes and ketones a b c d 1 acetaldehyde 2 acetone 3 acetophenone 1 acetaldehyde 2 acetophenone 3 benzophenone 1 acetone 2 acetaldehyde 3 formaldehyde 1 formaldehyde 2 acetaldehyde 3 acetone 7 22 What is the relationship between the following two structures a b c d tautomers stereoisomers resonance structures constitutional isomers but not tautomers 23 Which of the protons in the following molecule appear at the highest value in the 1H NMR spectrum a b c d i ii iii iv 24 What reactive intermediates are involved in the following reaction a b c d the cyclic chloronium ion derived from cyclohexene the trichloromethyl cation Cl3C the cyclohexyl carbocation the trichloromethyl anion Cl3C and dichlorocarbene Cl2C 8 25 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 9 ID A CH310N Exam I version 1 Answer …