3. Compare the following four reducing reagents NaBH4 vs LiAlH4 vs DIBAL vs H2, Pd/C and be specific on the scopes and products of each reagent. For example, reducing reagent XXX can reduce an aldehyde to a primary alcohol, etc. 4. Compare KMnO4, Na2CrO4, CrO3 vs PCC, DMP or Swern vs HIO4 oxidations. 5. Compare KMnO4 vs Ozonolysis cleavage:
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- 1-propanol (1.jpg up) 2-propanol (1.jpg down) Tertiary butyl alcohol (2.jpg) A recognition test will be made by making use of the difference in oxidation properties to 3 different alcohol given above. By what method is used, these alcohols can be separated from each other? Explain.. A colorless liquid, C4H6O, having a boiling point of 97-98°C was found to be soluble in water and also in ether. It gave a negative test for the presence of halogens, sulfur, and nitrogen. It did however, give a positive test to 2,4-dinitrophenylhydrazine reagent. It gave a negative result when treated with ceric nitrate solution and also Tollen’s reagent. Treatment with ozone followed by hydrolysis in the presence of zinc gave formaldehyde as one of the products. What is the structure and name of the colorless liquid?In which of the statements given below, the event is not an oxidation reaction? A. Product formation as a result of the reaction of benzoine with nitric acid B. Formation of the product as a result of the reaction of 2-propene at KMnO4 / Basic ambient temperature C. Formation of the product as a result of the reaction of 2-propene in KMnO4 / Basic medium cold D. CH3CH2OH + KMnO4 → CH3COOH E. Reaction of an alkyl halide with ammonia
- The sub-part that needs to be solved... 4. When propanal undergoes continued oxidation, it yields: A. Propanol B. Propanoic acid C. Propanone D. No reaction 5. The _______ test, also called the silver mirror test, involves a solution that contains silver nitrate (AgNO3) and ammonia (NH3) in water. A. Tollen's B. Benedict's C. Tollens D. BenedictsCompounds A, B, and C which are all alcohols are subjected to the Lucas test. An oily layer was formed almost instantly after the addition of reagents to Compound C. For compound A, it took several minutes before an oily layer was formed. Meanwhile, it took at least one hour with compound B before an oily layer was observed. What could be compound B? Choices: Ethanol Isopropyl alcohol tert-butyl alcoholThe addition of an alcohol to an acid chloride is an example of alcoholysis (alcohol addition with bond breakage). Consider the alcoholysis reaction below and answer the questions that follow. 1. Show the tetrahedral intermediate that is formed after the nucleophilic addition of the alcohol to the acid chloride. Be sure to include all lone pair electrons and formal charges on your intermediate structure. 2. Show the final product of this alcoholysis reaction that forms after the intermediate you made in Part 1. Do not include inorganic or charged products in your answer. Be sure to include all lone pair electrons and formal charges.
- In each case, show how you would synthesize the chloride, bromide, and iodide from the corresponding alcohol. (a) 1-halobutane (halo = chloro, bromo, iodo) (b) halocyclopentane (c) 1-halo-1-methylcyclohexane (d) 1-halo-2-methylcyclohexaneWe have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation? (a) the I in the DMP reagent (b) the carbinol C in the alcohol that is oxidizedIn which of the statements given below, the event is not an oxidation reaction? A. Reaction of an alkyl halide with ammonia B. Formation of the product as a result of the reaction of 2-propene at KMnO4 / Basic ambient temperature C. Formation of the product as a result of the reaction of 2-propene in KMnO4 / Basic medium cold D. Formation of the product as a result of the reaction of benzoine with nitric acid E. CH3CH2OH + KMnO4 ® CH3COOH
- For compound D to E, what is the reaction of a primary alcohol to an aldehyde and what can be the potential reagent? (reduction / oxidation / elimination / substitution) (mCPBA / PCC / CrO3 / LiALH4 with hydronium quench)Using the wittig reaction, synthesise aldehyde 4 to form cis alkene 2, and trans alkene 3. In your answer, with your choice of R group, describe synthetic routes to each alkene and include reagents and conditionsElimination of HBr from 2-bromonorbornane gives only 2-norbornene and no 1-norbornene. How do you account for the regioselectivity of this dehydrohalogenation? In answering this question, you will find it helpful to look at molecular models of both 1-norbornene and 2-norbornene and analyze the strain in each.