Midterm1_ReviewKey

Midterm1_ReviewKey - Chemistry 17 Review Session #1 Monday,...

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Chemistry 17 Review Session #1 Monday, October 16, 2006 Part 1: Andres Martinez Question 1 . (a) Provide the hybridization and bond angles for all C, N, and O atoms in the starting material and in the product of the following reaction. H 3 C O H NaCN H 2 O H 3 C OH C sp3, 109.5° sp3, 109.5° sp3, 109.5° sp3, 109.5° N sp2, 120° sp2, 120° sp, 180° sp, 180° sp3, 109.5° (b) How many resonances would you expect in the 13 C NMR spectra of the starting material and product? 3 13 CNMR resonances 4 13 CNMR resonances (c) What would be the main difference in the IR spectra of the starting material and product? IR will have sharp peak around 1700 cm 1 due to carbonyl IR will have broad peak around 3500 cm 1 due to alcohol Question 2. How many resonances would you expect in the 13 C NMR spectra of the following compounds? t -Bu H 3 C O NH 2 Et H 3 C CH 3 8 13 C NMR resonances 10 13 CNMR resonances
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Part 2: Miriam Quintal Question 1. For each of the following pairs of reactants: i) identify the nucleophile and electrophile ii) draw the curved arrow mechanism for the addition of the nucleophile to the electrophile iii) predict the product iv) draw and label the frontier molecular orbitals involved in the reaction (HOMO and LUMO) 1. O CH 3 CH 3 + Br 2. N + HF 3. CH 3 N H CH 3 + CN
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Part 3: Chris Uyeda Question 1. In water, fructose exists as an equilibrium mixture of the pyranose and furanose forms.
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Midterm1_ReviewKey - Chemistry 17 Review Session #1 Monday,...

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