CHE 241/240 Organic Chemistry Instructor: Dr. Dexter L. Criss Exam #3 (Learning Center Version) Student?s Full Name (Print) Student?s Full Name (Signature) NOTE: You are allowed to use calculators on this exam. However, sharing of calculators is strictly prohibited. Violators will receive a ?0? grade for the exam! NO PENS!!! Remember, no hats or caps are allowed during the exam! Good Luck!!! I. Nomenclature 8 points CH3CH2OH OH CH3 O O O OHO III. Which compound below would have the highest boiling point? Please explain your selection. 5 points Br Br CH3H3C II. Give the mechanism and product for the reaction below. 12 points V. Reactions. 35 points IV. Which alcohol is the stronger acid; methanol or ethanol? Explain your answer. 5 pts 1. 2. CH3 HBr BH3 H2O2 H2SO4 (Conc) CH2N2 heat CCl2 CH3 CH3 CH3 CH3 CH3 O C CH3 CH3 CH3 CH3 OH CH3 C CH3 CH3 H H HCC OCH3 CH3Cl CH3OH Hg(OAc)2 / H2O NaBH4 1. 2. CH3 C O O OH C C CH3H O3 HBr CH3 C C CH3 Br2 Br NaOH Water CH3 CH3 OH SOCl2 CH3CH2 O CH2CH3 H Br S O O CH3Cl OH KMnO4 / H2O Br2 cold O OHCH3 BrCH3 CH3 H3O + O3 KMnO4, H2O Heat NaH OH HBr MMPP C HH CH3 CH3 OH CH3 HO CH3Cl CH3 Br OMsCH3 1.NaH 2. CH3Br O3 2 moles HBr CH3 C C H Br CH3CH2CH2OH2 moles conc H2SO4 Cl CCl2 CH3 CH3 CH3 CH3 CH3 O C CH3 CH3 CH3 CH3 OH CH3 C CH3 CH3 H H HCC OCH3 CH3Cl CH3OH Hg(OAc)2 / H2O NaBH4 1. 2. HH OsO4 CH3CH2OH + HOCH2CH3 H3O + Br2 H2O (CH3)2CuLi VII. Draw the major product and mechanism for the reaction below. 10 points VI. Give a plausible mechanism for the reaction below. 12 points CH3CH2OH CH3CH2OH+ H2SO4 (conc) H2O CH3CH2 O CH2CH3 OH SOCl2 VIII. Write a retrosynthetic analysis that could be used to synthesize the product below from cyclohexane. 10 points CH2 Retrosynthesis Synthesis CHE 241 ONLY!!!!!! IXb. Compound A has the molecular formula C5H8 and shows a peak near 1650 cm-1 (moderate) in its IR spectrum. Compound A rapidly decolorizes liquid bromine. In addition, the compound is soluble in cold concentrated H2SO4. Treatment of A with hydrogen gas and nickle catalyst yields compound B (C5H10). Treatment of A with cold aqueous KMnO4 gave a diol C. However A gave a positive test with hot aqueous KMnO4. Propose a structure for A, B, C. 8 points CHE 240 ONLY!!!!!! IXa. 8 points H CH3 Br SO3 H2SO4 NO2 IR Table
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