CHE 232-1, Summer 2008Dr. HarrisName (please print)___________________________________Student ID #______________________________________Short Answer: (4 pts each)1) What type of information is provided by ultraviolet/visible spectroscopy? identifies different types of pi bonds and conjugation 2) What is the multiplicity of the labeled proton? multiplet of 9H3CH2CCH2H2COH3) How many peaks would you see for 2-pentanone in a proton NMR spectrum? 44) 2-pentene is reacted with HBr and peroxide. Draw the product.Br5) How many products would you get for the monochloronation of 2,2’-dimethylbutane? 3 Predict the Product. (4 pts. each)6)Br2ROORBr7)Cl2ROORClClClClCl8)NBShvBrBrBrBr9)Br2CCl4BrBr10) HBrBrMechanism: (Show all steps) (15 pts.)11)Br2CCl4BrBrBrBrBr BrBr+BrSpectroscopy: (15 pts. each)12) Using the MS, IR and +1H NMR spectra determine the formula and structure of the unknown compound.Molecular ion peak at 150 and 152.BrC5H11Br200Shift(ppm)3.398 triplet1.86 multiplet of 91.44 multiplet of 91.32 multiplet of 120.93 triplet13) Using the following data, give the formula and structure of a compound with C, H and O.- Molecular ion peak at 102.- IR peak at 2850-3000 cm-1.- protn NMR data has a doublet at 1.1 ppm. (12H) and a septet at 3.6 ppm. (2H) C6H14OO14) Give the structure and formula using the following spectra.Molecular ion peak at 87.C4H9NONOShift(ppm)2.077 22.98 1Exam Score1-5 _________ (/20)6-10_________ (/20)11 ________ (/15)12 _________ (/15)13 _________ (/15)14 _________ (/15)Total________
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