2004Final-Sorrell-1-11

2004Final-Sorrell-1-11 - Chemistry 35 Final 2004 Name_...

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Chemistry 35 Final 2004 Name__________________________________ SISD__________________________________ 1. (36 points) Determine whether the following reactions are correct as drawn. If the reaction is correct , write CORRECT in the box. If the reaction is incorrect , cross out the incorrect product (s) and draw the correct product(s) in the box. OH N Li N Br 2 CCl 4 Br Br CN NC CN CN Br NN CN CN + Bu 3 SnH OH H 2 SO 4 heat Cl PhCH 2 S - Na + SCH 2 PH
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Chemistry 35 Final 2004 Name__________________________________ SISD__________________________________ (1) Continued Br NaOMe MeOH (1) O 3 -78 C (2) Zn H 2 O OOO OH HO PBr 3 Br OH Cl S O pyridine 0 o C Cl Cl N O O Br RCO 2 -O 2 CR Br Br ++ HgSO 4 H 2 O H 2 SO 4 O
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Chemistry 35 Final 2004 Name__________________________________ SISD__________________________________ 2. (30 points) Indicate whether each statement is TRUE or FALSE. ______ (a) S N 2 reactions are first order ______ (b) S N 2 reactions proceed with retention of configuration ______ (c) S N 1reactions are favored with primary tosylates ______ (d) The relative stability of radical intermediates parallels that of carbocation intermediates ______ (e) Using the Cahn-Ingold -Prelog sequence rule an ethyl substitutent is higher priority than a vinyl ______ (f) A meso compound does not contain stereogenic centers ______ (g) A meso compound is chiral ______ (h) A polarimeter measures the magnetic properties of a molecule ______ (i) Resolution means purifying and separating mixtures of diastereomers ______ (j) A racemate contains an unequal mixture of enantiomers ______ (k) The overall rate of a reaction is proportional to G for the overall reaction ______ (l) Markonikov addition of H 2 O to an unsymmetrical olefin leads to the more highly substituted alcohol ______ (m) Diels-Alder reactions are concerted ______ (n) Chloride is a better nucleophile than iodide ______ (o) LDA is a weaker base than KOH
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Chemistry 35 Final 2004 Name__________________________________ SISD__________________________________ 3. (24 points) Provide structures for compounds with the following properties: (a) A chiral molecule of molecular formula C 3 H 8 O 2 containing two (2) hydroxyl groups (b) An achiral alcohol of molecular formula C 5 H 12 O 3 containing two (2) primary hydroxyl groups (c) A chiral alcohol of molecular formula C 6 H 14 O 3 containing three (3) primary alcohol groups (d) A molecule of molecular formula C 4 H 8 O that contains a cyclopropane ring and is achiral (e) A molecule of molecular formula C 8 H 7 NO that contains a benzene ring and is chiral Determine the degree of unsaturation (aka unsaturation index) of the molecules in (d) ______________ and (e) ______________
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This note was uploaded on 05/17/2008 for the course CHEM 0350 taught by Professor Suggs during the Spring '08 term at Brown.

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2004Final-Sorrell-1-11 - Chemistry 35 Final 2004 Name_...

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