Oxidation or Reduction - Introduction to Organic Chemistry - Quiz - Document's extract

Exams, Organic Chemistry

Description: Oxidation or Reduction, Following Observation, Undergoes Decarboxylation, Phenyl Selenium Halide, Electrophilic Reagent, Oxidize Cyclic Ketones, Unsaturated Ketones, Provide a Mechanism, Cope Elimination, Greatly Influenced. These are the important points of Introduction to Organic Chemistry.

CHEM 1. Classify each of the following reactions as either an oxidation or reduction (8 points). O H2 Cl deac. Pd O H a. b. OCH3 Na, NH3 EtOH OCH3 c. 1. OsO4 2. H2O2 OH OH O d. 1. N2H4 2. NaOH, ∆ 2. Explain the following observation (10 points)? O HCl H2O O CH3 CH3 (s)-enanteomer racemic 3. Which of the following undergoes decarboxylation (loss of CO 2 ) the easiest? reasoning (10 points). Explain your Docsity.com HO2C O CO2H O CO2H O A B C 4. Phenyl selenium halide (Ph-SeX) is an electrophilic reagent used to oxidize cyclic ketones to α,β – unsaturated ketones. Using the following scheme, provide a mechanism for this reaction (Hint: think Cope elimination) (12 points). O 1. LDA, -78 °C 2. Ph-SeCl 3. H2O2 O 5. Enolate formation is greatly influenced by both the choice of base and the temperature of the reaction. Given the following reaction conditions, predict the products that would be formed and Docsity.com provide an explanation for why each one is formed (12 points). O LDA -78 °C CH3 Br NaOCH3 25 °C 6. The Mannich reaction is a reaction that substitutes the α-carbon of a ketone with an amine. Propose a mechanism for the following Mannich reaction (8 points) O + H O H + H N HOAc O N 7. Determine the major product for the following reactions. Include a complete reaction mechanism with all appropriate stereochemistry (16 points). Docsity.com O O CH3 NaOH a. b. 1. O3, -78 °C 2. H2O2 8. Complete the following roadmap problem by giving the structures if the missing compounds (24 points). Docsity.com 1. O3 2. DMS A CF3CO3H B SOCl2 C AlCl3 O F (C17H20O) [(PPh3)CuH]6 E NaOH D [(PPh3)CuH]6 = Stryker's Reagent A: D: B: E: C: F: Bonus Docsity.com 1. In chapter 19, we discussed a variety of condensation reactions (aldol, claisen, etc.). These reactions are powerful in that they form carbon-carbon bonds fairly easily. The Knoevenagel condensation is a related reaction to those other condensat

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ion reactions. The reaction involves the condensation of a β-dicarbonyl compound and an aldehyde. Predict the product of the following series of reactions where the second step is a Knoevenagel condensation (10 points). O O + Ph OCH3 1. NaOCH3 2. benzaldehyde, H+ 2. The reaction of an α-haloketone with sodium hydroxide produces a carboxylic acid in a reaction known as the Favorskii rearrangement. The mechanism of the reaction includes the formation of an enolate followed by intramolecular nucleophilic addition. Using the below example, provide a mechanism for this reaction (15 points). O H3C Cl NaOH H3C O OH Docsity.com

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