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Chemistry
Posted 10 months ago

(a) Assign the configuration of the allene compound shown below. Ensure that you explain how you reached your answer.
[8 marks]
(b) Which of the following compounds 1-3 will undergo nitrogen inversion? Explain how you reached your answer and include a drawing illustrating the nitrogen inversion process.
1
2
3
[8 marks]
(c) Draw the two possible chair conformations for the substituted cyclohexane shown below. State which of the conformations is more stable and explain your reasoning.
[8 marks]
(d) Predict the structures of the product(s) and provide a mechanism for the following reaction. Use the solid/dash wedge convention to show three dimensions. Explain the stereochemical outcome.
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Answer from Sia
Posted 10 months ago
Solution
1
Determine the priority of the groups attached to the allene: For assigning the configuration of an allene, we need to look at the substituents attached to the terminal carbon atoms of the allene. The priority is assigned based on the atomic number of the atoms directly attached to the carbon atoms
2
Assign the configuration: The configuration of each end of the allene is determined by the Cahn-Ingold-Prelog priority rules. If the groups of higher priority on both ends are on the same side, the allene is assigned as (E)-configuration; if they are on opposite sides, it is assigned as (Z)-configuration
a Answer
[Insert the configuration of the allene compound here]
Key Concept
Assigning configuration to allenes requires considering the priority of substituents on the terminal carbon atoms.
Explanation
The configuration is determined by the relative positions of the highest priority groups on the terminal carbons of the allene.
Solution
1
Understand nitrogen inversion: Nitrogen inversion is a process that occurs in amines where the nitrogen atom is pyramidal and can invert to form a mirror image of the original structure. This process is rapid in amines that are not sterically hindered
2
Identify the steric hindrance: For each compound, assess the steric hindrance around the nitrogen atom. Compounds with less steric hindrance will undergo nitrogen inversion more easily
b Answer
[Insert which compounds will undergo nitrogen inversion and include a drawing]
Key Concept
Nitrogen inversion occurs more readily in amines with less steric hindrance around the nitrogen atom.
Explanation
Steric hindrance can prevent or slow down nitrogen inversion by making the energy barrier for inversion higher.
Solution
1
Draw the chair conformations: Sketch the two possible chair conformations for the substituted cyclohexane, placing the hydroxyl group in the axial position in one drawing and in the equatorial position in the other
2
Assess stability: Compare the two conformations to determine which has less steric strain and torsional strain, which will be the more stable conformation
c Answer
[Insert which chair conformation is more stable and why]
Key Concept
The stability of cyclohexane chair conformations is influenced by steric and torsional strain.
Explanation
The conformation with the hydroxyl group in the equatorial position is typically more stable due to less steric hindrance.
Solution
1
Identify the reaction: The reaction of an alkene with OsO4 typically leads to the formation of a diol through a syn addition, where both hydroxyl groups are added to the same side of the alkene
2
Predict the product: Use the solid/dash wedge convention to draw the product of the reaction, ensuring that the hydroxyl groups are on the same side of the former double bond
3
Explain the mechanism: The osmium tetroxide adds to the alkene to form a cyclic osmate ester intermediate, which is then reduced to form the syn diol
d Answer
[Insert the structures of the product(s) and the stereochemical outcome]
Key Concept
OsO4 reacts with alkenes to form syn diols.
Explanation
The reaction proceeds through a cyclic osmate ester intermediate, leading to the addition of hydroxyl groups to the same side of the alkene.

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