Organic Chemistry II
Organic Chemistry II CHEM 212
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This 9 page Study Guide was uploaded by Delbert Nikolaus PhD on Saturday October 3, 2015. The Study Guide belongs to CHEM 212 at Bucknell University taught by Staff in Fall. Since its upload, it has received 86 views. For similar materials see /class/218100/chem-212-bucknell-university in Chemistry at Bucknell University.
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Date Created: 10/03/15
NMR Practice Problems 1 Tell precisely how you would use the proton NMR spectra to distinguish between the following pairs of compounds a lbromopropane and 2bromopropane propanal and propanone ethyl acetate MeCOZEt and methyl propanoate EtCOZMe lbutyne and 2butyne 9po N V Each of the following compounds exhibits a single 1H NMR peak Approximately where would you expect each compound to absorb a cyclohexane b acetone c benzene d glyoxal ethandial e dichloromethane f trimethylamine CH33N 3 Draw structures for compounds that meet these descriptions a C2H60 one singlet b C3H7Cl one doublet and one septet c C4H8C120 two triplets d C4H802 one singlet one triplet and one quartet 4 The two spectra below are of phenol and benzaldehyde Assign them H mm 543 515 mu l l l l l a 7 5 5 a 3 2 1 u m 9 a 7 5 5 a 3 2 1 u 5 For each spectrum below chose between the alternative compounds Give your reasons or KOH Or an 75 m 55 En ss 5n as on 35 an 25 2D 15 u as nu W or M SD ss 5n as on 35 an 25 2D 15 u as nu 6 The spectra below are of acetone 12dichlor0ethane 112trich10r0ethane 22dimeth0xypr0pane 1 bromopropane and 2br0m0pr0pane Assign them a b 7 Assign the following spectra to one of the compounds listed 14 139 quot quot 14di 1 xy39ucu eue phenylethyne 3methyl3hydroxylbutyne 2bromobutane l2dibromo2methylpropane 8 Propose plausible structures for the ve compounds whose proton NMR spectra are shown a C4H1002 b C7H7BIquot C C4H9BIquot CgHgBl a b m M 6N m 8mmg 1F 1 100 600 300 201200 300 l ll l 0 d 5O 004 Im g J l J 201 100 603 501 200200 l l l l l l 3395 3IE 2395 ZIEI 1395 1IE EII5 EIIEI 75 7D 55 5D 55 5D 65 6D 35 3D 25 2D 15 1D D5 EIEI 9 Compound HC9H12 gives a proton NMR spectrum as shown below Assign a structure ll 5 00 100 604 Il 10 Two spectra are given below along with their molecular formulas Propose a structure that corresponds to each spectrum C3H7Cl 200 201 302 ll u 40 35 30 25 20 15 10 05 00 C9H1002 197 200 303 301 lg IA 65 60 55 50 45 40 35 30 25 20 15 10 05 00 11 The integrated 1H NMR spectrum of a compound of formula C4HlOO is shown Propose a structure consistent with the data 12 The compound whose proton NMR spectrum is shown below has the molecular formula C3H6Br2 Propose a plausible structure 13 A compound C10H1202 whose spectrum appears below was isolated from a reaction mixture containing 2phenylethnaol and acetic acid Propose a structure for this compound 14 The compound whose proton NMR spectrum is shown has the molecular formula C4H702Cl and shows an infrared absorption peak at 1740 cmAl Propose a plausible structure 15 A small plant was adding bromine across the double bond of 2butene to make 23dibromobutane A controller malfunction and allowed the reaction temperature to rise beyond safe limits A careful distallation of the product showed that several impurities had formed including the one whose NMR is shown below Determine the structure 45 An 35 an 25 2D 15 1D us an 16 When 2chloro2methylbutane is treated with a variety of strong bases the products always seem contain two isomers A and B of formula C5H10 When sodium hydroxide is used as the base isomer B predominates Determine the structures of A and B and explain the experimental results A 17 A new chemist moved into an industrial lab where work was being done on oxygenated gasoline additives Among the additives that had been tested she found an old bottle containing a clear pleasant smelling liquid but missing its label She took a quick NMR and was able to determine the identity of the compound without additional information Can you The proton NMR is shown below 158 ll 551 51 18 An allylic halide A of formula C5H9Cl undergoes Snl reaction with water to yield a mixture of two isomeric products B and C The proton NMR spectra of B and C are shown Suggest structures for A B andC 13 92 T 3 3T0 ii 052 105 056 300 l l l l ED 55 ED 45 AD 35 SD 25 ZEI 15 WEI DE EIEI C S 38 985 T 0 1w gJ l 052 054 051 300 l
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