Chemistry Workshops
1. All of the following reactions occur by analogous mechanisms. Write a single, general mechanism that explains all of these reactions. Make a table listing the electrophiles and the nucleophiles, reaction by reaction, for the first mechanistic step and also for the second mechanistic step.
RCH=CH2 + Cl2 ---> RCHClCH2Cl
RCH=CH2 + Cl2 (in H2O) ---> RCH(OH)CH2Cl
RCH=CH2 + Br2 ---> RCHBrCH2Br
RCH=CH2 + Br2 (in CH3OH) ---> RCH(OCH3)CH2Br
RCH=CH2 + HCl ---> RCHClCH3
RCH=CH2 + HBr ---> RCHBrCH3
RCH=CH2 + HI ---> RCHICH3
RCH=CH2 + H2SO4 ---> 
RCH=CH2 + H2SO4 (in H2O) ---> RCH(OH)CH3
RCH=CH2 + H2SO4 (in CH3OH) ---> RCH(OCH3)CH3
RCH=CH2 + Hg(O2CCH3)2 (in H2O) ---> RCH(OH)CH2-HgO2CCH3
RCH=CH2 + Hg(O2CCF3)2 (in CH3OH) ---> RCH(OCH3)CH2-HgO2CCF3
2. Propose structures for each of the lettered compounds. Show your reasoning. Two isomeric compounds, A and B, have the molecular formula C6H12. Both A and B react with H2 in the presence of Pt catalyst to give 2,3-dimethylbutane. When A is heated with a few drops of concentrated H2SO4, it is converted to a mixture of A and B in which B predominates.
3. An optically active compound, C6H10, was hydrogenated over a platinum catalyst to give an optically inactive hydrocarbon, C6H12, which was identical to methylcyclopentane. Give the structure of the optically active C6H10 compound and explain why this structure is uniquely consistent with the data. Carefully outline your logic.
4. Deduce structures for the unknown compounds based on the spectroscopic data provided.
(clicking on the spectra brings up a much larger image)
Materials adapted from:
Peer-Led Team Learning: Organic Chemistry, 1/e
Jack A. Kampmeier, University of Rochester
Pratibha Varma-Nelson, St. Xavier University
Donald Wedegaertner, University of the Pacific
Prentice-Hall, 2001, ISBN 0-13-028413-0
http://www.sci.ccny.cuny.edu/~chemwksp/OrganicChem.html