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 Question 1 2 3 4 5 6 Section II Value 15 16 12 15 8 9 75 Section I Raw Total 75 150 Grade Score UTID September 2011 CH310N Exam I 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 number of types of different protons in a compound a number of signals b chemical shift c integral d splitting 2 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 3 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 1 4 What is the splitting of the signal in the 1H NMR spectrum for the methyl protons of 1 bomo 2 methylpropane a singlet b nonet c triplet d doublet 5 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 6 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 and 2 only 3 and 4 only 2 and 3 only 1 2 and 3 2 7 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 8 What is the correct assignment of the names of the following ketones a b c d 1 acetaldehyde 2 acetophenone 3 benzaldehyde 1 acetone 2 phenol 3 benzaldehyde 1 acetone 2 acetophenone 3 benzophenone 1 formaldehyde 2 benzaldehyde 3 acetophenone 9 What is the hydrogen deficiency index for a compound with a molecular formula of C 10H16O2 a 1 b 2 c 3 d 4 3 10 What is the major organic product obtained from the following sequence of reactions a b c d 1 2 3 4 11 What is the major organic product obtained from the following sequence of reactions a b c d 3 methyl 2 butanol 3 methyl 2 butene 3 methyl 1 butanol 2 methylbutane 12 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 4 13 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 14 What is the major organic product obtained from the following reaction a b c d 1 butene 2 methyl 1 propanol 2 methylpropene 2 butene 15 What is the relationship between the following two structures a b c d resonance structures tautomers stereoisomers constitutional isomers but not tautomers 16 What is the major organic product obtained from the following reaction a b c d 1 2 3 4 5 17 Which of the following is the best choice of solvent for the formation of phenyllithium by the reaction of bromobenzene with lithium a ethanol b water c tetrahydrofuran d acetic acid 18 Which of the protons in the following molecule appear furthest downfield in the 1H NMR spectrum a b c d i ii iii iv 19 What is the major organic product obtained from the following reaction a b c d 3 phenylbutanone 3 phenyl 2 butanol propiophenone PhCOCH2CH3 2 phenyl 2 butanol 20 Which feature in the 1H NMR spectrum provides information about the number of neighboring protons of each proton in the compound a chemical shift b number of signals c integral d multiplicity 21 Which of the protons in the following molecule appear furthest downfield in the 1H NMR spectrum a b c d i ii iii iv 6 22 Which of the following mechanisms accounts for the acid base reaction of ethylmagnesum bromide with acetylene to give acetylide anion a b c d 1 2 3 4 23 Which of the following is not true regarding 1H NMR spectroscopy a for a particular proton is independent of the magnetic field strength of the instrument used b a downfield peak appears at a lower value of c deshielding leads to peaks at higher values of d on a 300 MHz instrument a proton that adsorbs irradiation at a frequency 900 Hz higher than the adsorption of TMS appears at 3 ppm 24 Which of the following bonds has the most ionic character a C Cu b C Li c C Zn d C Sn 25 What is the major organic product obtained from the following reaction a b c d E 2 butene E 2 iodo 2 butene 1 iodo 2 methylpropene methylcyclopropane 7 ID A CH310N Exam I Answer Section MULTIPLE CHOICE 1 2 …