CHEM 310 Exam 2Dr. HannaMarch 7, 2007Honor Pledge:In Part V of the Winthrop University Student Conduct Code, it is stated that “A fundamental tenet of all institutions of higher learning is academic honesty. … Misrepresentation of someone else’s work as one’s own is a most serious offense in any academic setting. … Academic misconduct includes but is not limited toproviding or receiving assistance in a manner not authorized by the professor in the creation of work to be submitted for academic evaluation including papers, projects, and examinations …”By my signature below, I pledge that I did not commit academic misconduct (cheat) on this examination.____________________________________ ______________________________Printed Name SignaturePart 1 _____________/15Part 2 _____________/15Part 3 _____________/20Part 4 _____________/20Part 5 _____________/15Part 6 _____________/15Total _____________/100Page 2Part 1: Nomenclature (15 pts)1a. Write IUPAC names for the following compounds (indicate stereochemistry where required):i) ii) iii) 1b. Draw structures corresponding to the following IUPAC names:i) meso-3,4-Dichlorohexaneii) m-FluorotolueneCH3C CCH3CHCH2CH2CH3CCHHCH2CH3BrNH2NO2NO2Page 3Part 2: Functional Group Identification (15 pts)Identify the functional groups present in the following compounds:O CH3OOOHAcetylsalicylic acid (Aspirin)ABOHNH CH3OAcetaminophenCDOFluorenoneEA = _________________________________B = _________________________________C = _________________________________D = _________________________________E = _________________________________Page 4Part 3: Stereochemistry (20 pts)3a. Identify the asymmetric centers in the following molecules and indicate the absolute configuration ((R)- or (S)-) of each asymmetric center:i) ii) 3b. Indicate the stereochemical relationship (enantiomers, diastereomers, or identical) of the followingpairs of compounds:i) andii) (2S, 4R)-dichlorohexane and (2R, 4S)-dichlorohexane3c. Draw a three-dimensional representation of (S)-3-methylpent-1-ene.CCCH2CCCH3CH3HHCH3HCCF3NH2CH3NHCH3OHCH3HHNHCH3HCH3OHHPage 5Part 4: Provide the Starting Material, Reagent, or Product (20 pts):Provide the missing piece (starting material, reagent(s), or product(s)) in the box provided.4a. 4b. 4c. 4d. 4e.KMnO4H+/H2OCH3OOHOCH2CHCH3CH3KMnO4H2OHNO3H2SO4OCH2CH3CH3H2Lindlar CatalystCH3CH3BrPage 6Part 5: Synthesis (15 pts)Provide a synthesis of each of the following compounds starting from benzene ( ) and/or acetylene (CH CH), and any other inorganic reagents or alkyl halides needed. Assume ortho- and para- isomers of disubstituted benzenes can be separated.5a. 5b. 5c. CH3CH3BrBrBrNO2OHOHO3SPage 7Part 6: Mechanisms (15 pts)Provide complete arrow-pushing mechanisms for the following transformations:6a. 6b. 6c.