Note for CHEM 262 at UMass
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Date Created: 02/06/15
1 Circle the compound which gives rise to the in 39ared spectrum below Ignore the absorption band at about 1820 cm39l See the last page for IR absorption information HJj 2 Use the 1HNMR spectral information to propose structures for each compound For partial credit draw structural 39agments that you conclude are in the molecule even ifyou cannot come up with a complete structure A table of chemical of chemical shift information is on the last page ofthe exam a C3HEBI CI 21 6 2 hydrogens quintet 5 lines 35 6 2 hydrogens triplet 37 6 2 hydrogens triplet b C4H7Cl3 09 6 3 hydrogens triplet 13 6 2 hydrogens sextet 6 lines 21 6 2 hydrogens triplet c CgH12 13 6 3 hydrogens triplet 23 6 3 hydrogens singlet 26 6 2 hydrogens quartet 71 6 4 hydrogens singlet d C7H150 11 6 6 hydrogens doublet 12 6 9 hydrogens singlet 326 1 hydrogen septet 7 lines 3 How many lines are observed for the signals of the hydrogens at the sites labeled a and b in the 1H NMR spectrum of the compound below Assume all coupling constants are equaL a1fora1forb b2fora2forb c2fora3forb d3fora3forb 4 How many lines are observed for the signals of the hydrogens at the sites labeled a and b in the 1H NMR spectrum of the compound below Assume all coupling constants are equaL O O a Y b O a4fora2forb b3fora5forb c2fora5forb d3fora3forb 5 How many kinds of chemically nonequivalent hydrogens are there in the compound below Cl a4 b5 06 d7 6 Which one ofthe compounds below would show only one signal a singlet in its NMR spectrum 0 0 H OH A0 0 lt gt o A B c D 7 Draw a structural formula for a 2methyl3pentanol b the alkyl halide and aldehyde or ketone that could be used in a Grignard synthesis of 2methyl3pentanol 8 Write a mechanism forthe reaction below CH3 CH3 H O HCI gt 2 OH Cl 9 Specify whetherthe reactions shown below proceed via net oxidation 0 of carbon net reduction R of carbon or neither N net oxidation nor reduction of carbon 0 O OH OH 3 o NH2 0 OH 0 o o o b gt HO OH HO OH 002 OH O 10 Specify the reagent you could use to carry out each of the reactions below in good yield OH OH 3 gt o 0 OH b H30 H30 H29 H30 11 Circle the structure which depicts most accurately the major electrostatic interaction between two molecules of liquid ethanol HOng CH 5 0 a g 2 3 b l7l CHZCHs 60 CH3CH2 H 3 H CH2CH3 O 5HOCH CH CH CH 5 H C 2 3 3 2O 5 0 d l 39 CH3CH2 H CHscH2H 12 Draw structural formulas for the Grignard reagent and the aldehyde or ketone that together could be used in a Grignard synthesis of the compounds below a A CHZOH HO b ltCH2CH3 CHZCH3 13 Draw a structural formula for the major organic product of the following reactions OH 8 H2804 CEN Brz b FeBr3 14 The following transformation may be accomplished in two steps Write the reagents you would use in each step over the appropriate arrows lgt O gt gt gtBr step1 step2 NMR Chemical Shift Information Typeof Hydrogen Chemical shift g1 Type of Hydrogen Chemical 0 H m d a kyl primary CH3 07 13 alcohol C 195 39 bl alkyl secondary CH2 12 16 varla e H alcohol ether 0 H aklyltertiary C 1418 C 33 45 H II I39 C 39 I39 C a ylc 1622 VInyIc 4565 CH O aromatic Ar H 6580 methyl ketone 20 24 CH3 aldehyde c 97 H 100 aromatic methyl Ar CH3 24 27 11 X H carboxylic acid C 11 0 H 39 alkylhallde C 2540 O 120 X Cl Br I Infrared Absorption Information Structuralm Freguency m4 Structuralm Freguenc m4 OH 3300 3650 strong broad alcohols ROH CEO akynes 210072260 o H 2500 3500 strong broad o med39um carboxyllc aCIds R002H C 1670 1790 strong C H alkyne C H 3300 strong carbonyl group of carboxylic acids aldehydes C H a39kene C H 30203100medlum ketonesy esters C H a kyl groups 28502960 medium cc a kenes 1640 1680 medium
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