2005 Organic Chemistry CHE230-001 EXAM 2 KEY Page 0 of 6 1. Use the figure below to answer all the questions in 1a-e. IIIBr I I(a) (b) (c)(d) (e) (f) a. (2 pts.) Which molecule above will undergo SN2 fastest? (8 pts.) Provide a brief reason for your answer. _________________________________________________ _____________________________________________________________________________________________________________________________________________________________________________________________________________________ b. (2 pts.) Which molecule above will undergo SN2 slowest? ____ (8 pts.) Provide a brief reason for your answer in 1c. ___________________________________________ ______________________________________________________________________________________________________________________________________________________________________________________________________________________________ c. (10 pts.) Name 1e. Stereochemistry is involved! _____________________________________________________________________________________________________________________________________________2005 Organic Chemistry CHE230-001 EXAM 2 KEY Page 1 of 6 d. (2 pts.) Pick the reactant that will undergo SN1 the fastest. ____ (8 pts.) Provide a brief reason for your answer. _______________________________________________ _____________________________________________________________________________________________________________________________________________________________________________________________________________________ e. (2 pts.) Which molecule above will undergo SN1 slowest? ____ (8 pts.) Provide a brief reason for your answer. ________________________ __________________________________________________________________________________________________________________________________________________________________________________________________________________ 2. How are the pairs of structures below related? a. (10 pts.) BrBrHH2a1 2a2 They are ________________________ . b. (10 pts.) 2b1 2b2BrBr They are __________________________ .2005 Organic Chemistry CHE230-001 EXAM 2 KEY Page 2 of 6 3. Use the equation below and the following description to answer the following questions. * The chlorobromocyclohexene reactant is optically active, but the mixture of products is not. * Four stereoisomers with the formula given were found in a ratio of 15:15:35:35. BrClC9H15OCl+ HBrCH3OH a. (5 pts.) Give the name of the mechanism of this reaction. ________________ b. (3 pts.) Calculate the degrees of unsaturation in the products; it is the same for all four. Also, see next page!2005 Organic Chemistry CHE230-001 EXAM 2 KEY Page 3 of 6 c. (12 pts.) Draw the four stereoisomers of C9H15OCl above. 4. (10 pts.) Draw an E2 product of the molecule below. There is stereochemistry to consider. You will not get full credit unless you include stereochemistry in your answer. HBrH | | | | | ----------------------------------------------------------------|-|------------------------------------------------------------- | | | | |
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