Question

1. In this question, we will explore the mechanism of the reaction between benzaldehyde and malonic acid to form cinnamic acid. 1. First, we will add malonic acid and pyridine to our reaction vessel. Draw a reasonable reaction mechanism that shows how malonic acid is converted to its reactive intermediate, called an enolate. 2. Next, we add benzaldehyde and piperidine. Before they interact with the enolate we formed in part 1, they must first come together to form a new reactive intermediate, called an iminium ion. Draw a reasonable reaction mechanism for this transformation. 3. Now show how the two reactive intermediates come together to form cinnamic acid, the product for Part 1 of this experiment. Hint: CO2 gas is lost during this process, which you will observe in lab! 4. If iminium is the reactive electrophilic species and not the aldehyde, what conclusion can you make about their relative electrophilicity?

          1. In this question, we will explore the mechanism of the reaction between benzaldehyde and malonic acid to form cinnamic acid.
1. First, we will add malonic acid and pyridine to our reaction vessel. Draw a reasonable reaction mechanism that shows how malonic acid is converted to its reactive intermediate, called an enolate.

2. Next, we add benzaldehyde and piperidine. Before they interact with the enolate we formed in part 1, they must first come together to form a new reactive intermediate, called an iminium ion. Draw a reasonable reaction mechanism for this transformation.

3. Now show how the two reactive intermediates come together to form cinnamic acid, the product for Part 1 of this experiment. Hint: CO2 gas is lost during this process, which you will observe in lab!

4. If iminium is the reactive electrophilic species and not the aldehyde, what conclusion can you make about their relative electrophilicity?

1. In this question, we will explore the mechanism of the reaction between benzaldehyde and malonic acid to form cinnamic acid.
1. First, we will add malonic acid and pyridine to our reaction vessel. Draw a reasonable reaction mechanism that shows how malonic acid is converted to its reactive intermediate, called an enolate.

2. Next, we add benzaldehyde and piperidine. Before they interact with the enolate we formed in part 1, they must first come together to form a new reactive intermediate, called an iminium ion. Draw a reasonable reaction mechanism for this transformation.

3. Now show how the two reactive intermediates come together to form cinnamic acid, the product for Part 1 of this experiment. Hint: CO2 gas is lost during this process, which you will observe in lab!

4. If iminium is the reactive electrophilic species and not the aldehyde, what conclusion can you make about their relative electrophilicity?

Added by Edward J.

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