Departmental Final Examination Organic Chemistry II 2425 NH2 N N OO P O O O H H OH OH H H 1 O ORGANIC CHEM 2425 Sample FINAL EXAM DIRECTIONS A periodic table is attached at the end of this exam Please answer all questions in the space provided as completely and clearly as possible Please show all your work for the writing portions of the exam PART I Multiple Choice 2 points each 1 How many set of equivalent hydrogens are present in the 1H NMR spectrum of 1 bromobutane A 1 B 2 C 3 D 4 2 Which of the following would give a 1H NMR which consists of a 9 H singlet at 1 30 and 5 H singlet at 7 30 A o CH2 CH2 CH3 CH3 C O B CH3 CH2 C CH3 3 D CH2O CH3 O 3 A compound exhibits a strong broad band in its IR spectrum centered about 3300 cm 1 Which type compound is more likely to be A Ketone B Alcohol C Alkene D Ether 4 Which species is are aromatic H N A I only IV III II I B IV only C II III and IV D II 5 Which of the following is incorrectly named OH B A D C A toluene B phenol C naphthalene D m xylene 6 Which is the electrophile generated in the nitration of benzene by mixture of nitric acid and sulfuric acid A NO B NO2 C HSO4 D NO3 7 Which of these are ortho para directors A NO2 B OCH2CH3 C CO NH2 2 D CO CH2 CH3 8 Which is the major product from this reaction OH i NaH 2 CH3I ether OCH3 I A D C B 9 Which of the following has the lowest boiling point A 1 pentanol B 2 pentanol C 3 pentanol D t butyl alcohol 10 Which compound s is are considered to be tertiary alcohol OH OH OH OH A only II III II I B I II IV C only IV D I III 11 Which is the major initial pair of products when methylisopropyl ether is treated with HI A methanol and isopropyl alcohol C methyl iodide and isopropyl alcohol B methanol and isopropyl iodide D methyl iodide and isopentyl iodide 12 Which of the following reagents is least likely to oxidize aldehydes A Air B PCC C Tollen s reagent D Chromic acid 13 Which of the following is Acetaldehyde O O A H C CH3 B H C H O O O O C CH3 C C H D H C C H 14 Which is the correct name for A acetophenone CO CH3 B benzophenone C phenone D phenyl ketone 15 Carboxylic acids have higher boiling points than alkenes of similar molecular weights Which of the following best explains this observation A vanderwaals interaction C higher pKa values B hydrogen bonding D all of these 3 16 Which of the following is least acidic A CH3 CHCl COOH B ClCH2 CH2 COOH C CH3 CCl2 COOH D BrCH2 CH2 COOH 17 What type compound is this O O A Lactone B Lactam C anhydride D Crown ether 18 What is the reagent for the following reaction O CO NH2 A Br2 OH H2O B LiAlH4 H3O O CH2 NH2 C Zn H3O D SOCl2 H3O 19 Which of theses is are a secondary amine s I CH3CH2 3N II CH3CH2 3 C NH2 A II and III B II only III CH3 NH CH2CH3 C III only D none of these 20 Which of the following is the strongest base H2N H2N A NH2 B NO2 C NH2 D OCH3 OCH3 PART II Nomenclature and structures 2 points each 21 Give the correct IUPAC names for the following structures a COOH H3C NO2 b CH 2 CH OCH3 c CH3 CH2 CH CO CH3 NH2 4 22 Give the correct structure for the following names a 4 chloro 2 5 dinitrophenol b p bromotoluene c cis 4 methylcyclohexanol PART III Comparison 2 points each 23 Identify assign the following as I Tautomer isomers T or geometrical isomers G O and OH II Enol E or ketone K O III Nitrile N or amide A NH2 C O IV Enamine E or amine A NH2 V Enantiomer E or Diastereomer D H Cl Cl H CH CH CH CH H COOH H COOH PART IV Synthesis 3 points each 5 24 Show by a series of reactions how you could prepare the following compounds from the indicated starting compound Be sure to clearly indicate the reagents used in each step I Benzene II p nitrobenzoic acid CH CH CN PART V Reactions 2 points each 25 Give the major organic product s of each of the following reactions Please show all relevant stereochemistry a NO2 CH3Cl AlCl3 b OH SOCl2 H c O Ag2O H2O H NH4OH OH d NO2 SnCl2 H3O OH NO 2 e NH2 HNO2 H2SO4 f 6 CH3 1 KMnO4 2 H3O CH2CH3 g CH3 POCl3 pyridine OH h CH3 i KMnO4 Br2 H3O FeBr3 OH NaOH H2O Cl j CN CN PART VI Mechanisms 4 points 26 For the following reaction write a complete mechanism for reaction which adequately accounts for the formation of product Show all intermediate structures and all electron flow using the curved arrow convention CH3 CH3 a AlCl3 CH3 CH3 C CH2Cl CH3 CH2 C CH3 b CH3 HBr 7 CH3 O CH3 PART VII Spectroscopy problems 8 points 27 a Which structure from the list below fits the IR spectra shown below 2 points b The mass spectrum of a compound shows a molecular ion at m z 113 the IR spectrum has 8 characteristic absorptions at 2270 and 1735 cm 1 and the 1H NMR spectrum shown below 4 points I Based on the mass spectral data and the IR data what functional groups are present in this compound II How many types of nonequivalent protons are there in this molecule III Propose a structure for this compound c Consider the data below to answer the following questions C8H7ClO IR 1690 cm 1 2 points 9 I Calculate the degrees of unsaturation for this compound II Propose a structure for this compound PART I Multiple Choice 2 points each 1 D 2 C 3 B 4 B 5 D 6 B 7 B 8 B 9 D 10 A 10 11 C 12 A 13 A 14 A 15 B 16 D 17 A 18 B 19 C 20 B PART II Nomenclature and structures 2 points each 21 a 3 Methyl 2 nitrobenzoic acid b Methyl vinyl ether c 3 Amino 4 methyl 2 hexanone 22 a Cl O2N NO2 HO 4 chloro 2 5 dinitrophenol b Br p bromotoluene c HO cis 4 methylcyclohexanol PART III Comparison 2 points each 23 I T II K III A IV E V D PART IV Synthesis 3 points each 11 24 I CH3Cl AlCl3 CO2H KMnO4 HNO3 H2SO4 H2O O2N O2N II CH2 Br NBS NaCN PhCO2 2 CCl4 DMF CH2CN PART V Reactions 2 points each 25 a NO2 CH3Cl No Reaction AlCl3 …