CHEM 346 EXAM 1 February 21 2012 Name Instructions This is a one hour exam which you will have two hours to complete You are only allowed to use molecular model kits scratch paper and your brain Good luck Chem 346 Exam 1 2012 24 16 15 Question 3 Question 4 Question 2 Question 1 The following list of reagents may be of use to you for this exam Question 7 Question 6 Question 5 TOTAL 10 12 13 10 100 AlCl3 Br2 Cl2 Cu I CuBr CuCl CuCN Et3N FeBr3 FeCl3 H2 HBF4 HCl H2NNH2 HNO3 H2O H3PO2 H2SO4 KI KMnO4 Mg0 MnO2 Na2Cr2O7 NaCN NaNH2 NaNO2 NaOCH3 NaOH Pd C Pd PPh3 4 P2O5 Pt C Sn0 SOCl2 Zn Hg h Chem 346 Exam 1 2012 1 Describe each of the following transformations as an oxidation reduction or neither and explain your designation based on labeling the oxidation levels of the carbons involved in the transformation 3 points each A I O Reaction classification B Reaction classification C O OH H3C Reaction classification D OH O Reaction classification E O Cl HO CH3OH Reaction classification I Br Br O OH OH H3C OH OH H3CO Cl H3CO H3CO Chem 346 Exam 1 2012 2 Predict the product s of the following transformations 8 points each A 1 SOCl2 2 H3CO AlCl3 3 KMnO4 O OH O OH 1 HNO3 cat H2SO4 2 CH3CH2OH cat H 3 Cl2 FeCl3 NO2 1 Br2 FeBr3 2 NaOCH3 3 Pd C H2 B C F Chem 346 Exam 1 2012 3 Provide reagents conditions for executing the following synthetic sequence You may assume that you can separate ortho and para isomers Each arrow should have one set of reaction conditions this doesn t include workups 8 points each A OH O B O O Cl CN O O Chem 346 Exam 1 2012 4 The following reaction was conducted and two products of electrophilic aromatic substitution were observed Based upon your knowledge of brominations show the two products that were formed with a clear explanation of the selectivity of these two molecules over all other potential EAS products 10 points Br2 OMe Chem 346 Exam 1 2012 5 Provide a synthesis of compound A from benzene B using reagents and conditions that we have discussed in lecture You may assume that you can separate ortho and para isomers 12 points F from NO2 A B Chem 346 Exam 1 2012 6 Provide an arrow pushing mechanism for the following transformation Writing proton transfer for the applicable processes is ok 13 points HO OH O O O O O O O O Chem 346 Exam 1 2012 7 In class we discussed the use of thionyl chloride SOCl2 to convert carboxylic acids to acid chlorides Another reagent that is capable of this same transformation is oxalyl chloride COCl 2 drawn below Based upon your knowledge of the thionyl chloride reaction provide an arrow pushing mechanism for the reaction below illustrating the effectiveness of this reagent for enabling this transformation Writing proton transfer for the applicable processes is ok Hint think about the byproducts 10 points O OH O Cl Cl O oxalyl chloride O Cl byproducts Chem 346 Exam 1 2012 Additional scratch paper Chem 346 Exam 1 2012 Additional scratch paper Chem 346 Exam 1 2012 Additional scratch paper