Chem 210- W07exam2key - Name Page 1 A When...

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Name _______________________ Page 1 1. (23 points) When 3-chloro-1-propene is treated with a strong base, a small amount of cyclopropene is formed. This transformation could be predicted to occur in two steps that are familiar to you: a proton transfer, followed by an intramolecular substitution. C C C Cl H H H NH 2 Follow the progress of this proposed transformation by providing the missing information (b) Estimate the Keq for the first reaction, and provide the curved arrows for the formation of the final products shown. (a) Provide the curved arrow mechanism for the first reaction that leads to the formation of the compounds shown at right. A. 4 6 B. Predict the products (or anything else requested) in the following reactions. Cl N H H H H H Na C C C H H H H Na C C C Cl H H H H H NH 2 Na C C C Cl H H H H N H H H Na Keq = 10 0 = 1 4 pts arrows, 2 pts Keq Cl N H H H C C C H H H H Na (c) Draw a complete transition state structure for this second reaction. δ 2 partial bonds 4 1 pt each charge HC HC C Cl δ H H C C C Cl H H H H H N C C C N(CH 3 ) 3 H H H H H Cl CH 3 OH H 2 SO 4 (cat) C C C H H H H (ii) a) draw the most unstable reactive intermediate predicted to form in this reaction (i) b) draw the final uncharged product(s) C C C H H H H C C C H H H H H H OCH 3 3 3 3 3-chloro-1-propene cyclopropene CH 3 H 3 C CH 3
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CH 3 Name _______________________ Page 2 II. (24 points) A. HO (a) Draw the two chair conformations for Compound D. Your drawings should clearly show both axial and equatorial positions for any ring atoms that have substituents ( be clear in your bond angles! ). OH CH 3 OH CH 3 CH 3 Compound D (b) Given that hydrogen bonding does not contribute substantially to the conformational stability of Compound D, estimate the Δ G˚ for the chair to chair conformational conversion represented by your drawings above by choosing the best answer: Δ as drawn above 12 2 B.
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