CHEM 310 Final Exam Dr. Hanna April 30, 2007 Honor 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 to providing 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 Signature Part 1 _____________/35 Part 2 _____________/35 Part 3 _____________/30 Part 4 _____________/60 Part 5 _____________/20 Part 6 _____________/20 Total _____________/200Page 2 Part 1: Nomenclature and Functional Groups (35 pts): 1A. Draw structures corresponding to the following IUPAC names (4 pts each): i) (E)-3-Methylpent-2-ene ii) 1,3-Diphenylpropan-2-one iii) Ethyl hexanoate 1B. Write IUPAC names for the following compounds (indicate stereochemistry where required, 5 pts. each): i) ii) iii) CCO2HFCH3CH2CH2CH3BrOHCH3OC(CH3)3Page 3 1C. Propose structures for molecules that fit the following descriptions (2 pts. each): i) An amide containing 4 carbons ii) An alkyne containing 5 carbons iii) A cycloalkene with a trisubstituted double bond iv) A secondary alkyl halidePage 4 Part 2: Structure, Bonding, Stereochemistry, Conformational Analysis (35 pts): 2A. Provide the hybridization of and the approximate bond angles around the circled atom in the following molecules or ions: (4 pts each): Hybridization Bond Angle i) ii) iii) 2B. Indicate whether the compounds in each pair are identical, constitutional isomers, enantiomers, or diastereomers. (3 pts. each): i) ii) iii) CH3C+CH3CH3CNCH3CH3ClClCOHOHOHCH3OOandCOHOHOHCH3OOCH3CH3CH3OHHandCH3CH3CH3HOHCH3HHSHHHSHCH3andPage 5 2C. The benzyl cation is a resonance stablized intermediate in many organic reactions. Draw three additional resonance forms for the benzyl cation (6 pts): CH2+ Benzyl Cation 2D. Circle the more stable conformation in each pair and explain your answer (4 pts each): i) ii) CH3CH3CH3HHCH3CH3CH3HHororHHHHHHHHHHHHPage 6 Part 3: Acids and Bases; Structure/Reactivity Relationships (30 pts): 3A. Circle the stronger acid in each pair and explain your answer: (4 pts each): i) ii) iii) iv) 3B. Rank the following compounds in order of reactivity toward nucleophilic acyl substitution (1 = fastest, 3 = slowest) (4 pts): OClOOCH3ONHCH3A B C CH3OHOorCHOHOBrBrOHCH3orOHCH3ClHIHorOHOCH3CH3orOHCH3CH3CH3Page 7 3C. Rank the following compounds in order of SN1 reactivity (1 = fastest, 4 = slowest). Explain your answer (5 pts): CH2CH2CH2CH2BrCH3CH3BrBrCH3CH3CH2CBrCH3CH3A B C D 3D. Rank the following compounds in order of SN2 reactivity (1 = fastest, 4 = slowest). Explain your answer (5 pts.): OHA B C DBrClIPage 8 Part 4: Provide the Reagent(s) or Product(s) (60 pts): i) ii) iii) iv) v) vi) CCCH3OCH3HHH2PdCH3CH3+H ClCH3OHOCH3OHCH2CH3CH2CH3KMnO4H+/H2OCH3CH3CH3CH3OCH3CH3CH2MgBr1. 2. H3O+OPage 9 vii) viii) ix) x) xi) xii) OOFCH3H+OH2CH2OHSCH3COHS CH3CH3CH3CH3CH3ClOAlCl3CH3ICH3SHO1) NaBH42) H3O+CH3CH3CH3OCl+2 (CH3)2NHPage 10 xiii) xiv) xv) OOHFCH3CH2OHH+OOHFOClFC C CHCH3CH3CCCHCH3CH3HHPage 11 Part 5: Reaction Mechanisms (20 pts): 5A. Provide complete arrow-pushing mechanisms for the following transformations (5 pts. each): i) ii) iii) 5B. When (R)-3-methylhexan-3-ol is heated in aqueous acid (H3O+), racemic 3-methylhexan-3-ol is formed. Propose an explanation (5 pts.). CH3CH3ClClHCH3O CH3CH3BrHOHCH3CH3CH3Br+CH3CH3I+CH3CH2+NaINaOH+OH2Page 12 Part 6: Synthesis (20 pts): Propose a synthesis of each of the following compounds starting from the indicated compound and any other reagents you need (5 pts. each): i) ii) iii) iv) CH3CH3OOHCH3CH3NH2CH3CH3OHCH3CH3OHBrOOHO