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Worksheet4-key-1 - Week 6 Discussion Worksheet#4 Answer Key...

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Week 6 Chem 51B - Jarvo Discussion Worksheet #4: Answer Key 1. For each of the following reactions below, draw the major product. Assign the absolute configuration of each starting material and product. Me Et O H HCl a. b. O NaOH c. Me O Me BrMg Cl Et OH H Me OH OH Me OH Me ( R) ( R) ( R ) ( R ) ( R) ( R ) ( S) ( R) Me Me Me Me ( S) ( S ) inversion but priorities change! Br 1. Li 0 2. Cu I organocuprate + Li I O Ph ( R ) OH ( S ) d. Cu Li
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Week 6 Chem 51B - Jarvo 2. Circle the bond that will have the IR stretch at the highest frequency. Provide a brief explanation for your choice. For IR, in analogy to Hooke’s law: Frequency wavenumber 1/mass of atoms and Frequency wavenumber bond strength These are competing effects and we have to decide which one dominates. Usually mass of atoms dominates. a) O-H or O-D To compare the stretches of C-H vs C-D bonds: Mass of D approx 2*mass of H Bond strengths: C-H approx 103 kcal/mol and C-D approx 104.5 kcal/mol. Therefore, the difference in masses is much larger and that effect dominates – the C-D has a stretch at lower frequency.
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