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

Exams, Organic Chemistry

Post: January 1st, 2013
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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

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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 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

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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).

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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).

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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

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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 condensat
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

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