Oxidation or Reduction - Introduction to Organic Chemistry - Quiz, Exercises for Organic Chemistry. Agra University
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shabo-rani1 January 2013

Oxidation or Reduction - Introduction to Organic Chemistry - Quiz, Exercises for Organic Chemistry. Agra University

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Oxidation or Reduction, Following Observation, Undergoes Decarboxylation, Phenyl Selenium Halide, Electrophilic Reagent, Oxidize Cyclic Ketones, Unsaturated Ketones, Provide a Mechanism, Cope Elimination, Greatly Influen...
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CHEM1. Classify each of the following reactions as either an oxidation or reduction (8 points).

a. Cl

O

H

O H2

deac. Pd

b. OCH3OCH3 Na, NH3

EtOH

c. OH

OH

1. OsO4

2. H2O2

d. O

1. N2H4

2. NaOH, ∆

2. Explain the following observation (10 points)? O

CH3

O

CH3

HCl

H2O

(s)-enanteomer racemic

3. Which of the following undergoes decarboxylation (loss of CO2) the easiest? Explain your

reasoning (10 points).

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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 O1. LDA, -78 °C

2. Ph-SeCl 3. H2O2

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

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provide an explanation for why each one is formed (12 points).

CH3

O

Br

NaOCH3

25 °C

LDA

-78 °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

O

HH

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).

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a. O O

NaOH

CH3

b. 1. O3, -78 °C

2. H2O2

8. Complete the following roadmap problem by giving the structures if the missing compounds

(24 points).

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1. O3

2. DMS A B C

DE

SOCl2

AlCl3

NaOH

CF3CO3H

[(PPh3)CuH]6

[(PPh3)CuH]6 = Stryker's Reagent

F (C17H20O)

O

A: D:

B: E:

C: F:

Bonus

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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 condensation 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).

Cl

O H3C NaOH

OH

OH3C

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