14D_w10_e01_key

14D_w10_e01_key - Chemistry 14D Winter 2010 Exam 1...

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Chemistry 14D Winter 2010 Exam 1 Solutions Page 1 Statistics : High score, average, and low score will be posted on the course web site after exam grading is complete. The exam is ready to be picked up when these numbers are posted. Some questions have more than one answer, even though only one answer may be listed here. To see the projected course grade cutoffs, consult the grading scale on the Chemistry 14D course web page. 1. CH 3 Cl CH 3 I I CH 3 I δ Cl δ H Better transition state structure: CH 3 I δ Cl δ H The cyclohexane ring is in a boat- like conformation before it flips into a chair. 2. Rate = k CH 3 Cl [NaI] 3. CH 3 I NaI acetone CH 3 I 4. The reaction of question 3 is faster because iodide ion is a better leaving group than chloride ion. It is possible for the nucleophile and leaving group to be the same. If you doubt this, ask yourself why they cannot be the same . 5. I CH 3 OH OCH 3 + OCH 3 Mixture of enantiomers
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Chemistry 14D Winter 2010 Exam 1 Solutions Page 2 6. Ph I rds Ph HOCH 3 Ph OCH 3 H HOCH 3 Ph OCH 3 Ph Ph HOCH 3 Ph OCH 3 H HOCH 3 Ph OCH 3 7. Cl CH 3 NaOCH 3 CH 3 OH CH 3 + CH 2 Major Not major 8. Cl
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14D_w10_e01_key - Chemistry 14D Winter 2010 Exam 1...

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