14D_w09_finalA_key

14D_w09_finalA_key - Chemistry 14D Winter 2009 Final Exam...

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Chemistry 14D Winter 2009 Final Exam Part A 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 final course grade cutoffs, consult the grading scale on the Chemistry 14D course web page. 1. (a) (b) (c) (d) (e) 2. This molecule is the weakest electrophile because carbon and sulfur have equal electronegativity, and the C=S bond has little δ + charge. 3. 4. The molecule circled in question 3 undergoes the fastest addition reaction because it has less steric hindrance (or less resonance to lose or less electron donating groups). The molecule circled in question 3 undergoes the fastest addition reaction because it has more δ + C=O. 5. Aldehydes do not undergo carbonyl substitution reactions. O O O 1. CH 3 MgBr (excess) 2. H 3 O + HO HOOC CH 3 CH 3 O H C C H 3 C OH C C 1. H 3 C 2. H 3 O + 1. LiAlH 4 2. H 2 O H N(CH 3 ) 2 O O HO N(CH 3 ) 2 Cl O N(CH 2 CH 3 ) 2 O NaSCH 3 DMF H 3 CS O N(CH 2 CH 3 ) 2 O H 3 CO OCH 3 O O 1. NaOCH
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14D_w09_finalA_key - Chemistry 14D Winter 2009 Final Exam...

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