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Part 2. Synthesis of an Ester. Esters are compounds of the form RCOOR'. They occur naturally in many plants and animals, and can be synthesized. They have a pleasant aroma usually described as "fruity" or "flowery". In a Fisher esterification, an ester is formed from the reaction of a carboxylic acid and an alcohol with a strong acid as a catalyst. The OH contained in the carboxylic acid group is replaced with the alkoxy group (O-R') from the alcohol, and an ester and water are formed. O O | || R—C—O—H + H—O—R' ? R—C—O—R' + H2O Questions Oil of Wintergreen: 1. Draw the chemical reaction between salicylic acid (the limiting reagent) and methanol. • Box the major functional group of each organic compound. • Write the formula of the catalyst in the box above the reaction arrow. Salicylic acid + Methanol ? catalyst Methyl salicylate + Water Functional Group: _____ _ _____ 2. What are two uses of methyl salicylate? 3. Comment on the toxicity of methyl salicylate. What is considered a lethal dose, and what is its uptake avenue (inhalation, skin contact, ingestion, etc.)? 4. Why is the mixture reacted with a sodium bicarbonate solution? Write the reaction. It does NOT react with the limiting reagent since limiting reagents are completely consumed.

          Part 2. Synthesis of an Ester.

Esters are compounds of the form RCOOR'. They occur naturally in many plants and animals, and can be synthesized. They have a pleasant aroma usually described as "fruity" or "flowery".

In a Fisher esterification, an ester is formed from the reaction of a carboxylic acid and an alcohol with a strong acid as a catalyst. The OH contained in the carboxylic acid group is replaced with the alkoxy group (O-R') from the alcohol, and an ester and water are formed.

O O
| ||
R—C—O—H + H—O—R' ? R—C—O—R' + H2O

Questions Oil of Wintergreen:

1. Draw the chemical reaction between salicylic acid (the limiting reagent) and methanol.
• Box the major functional group of each organic compound.
• Write the formula of the catalyst in the box above the reaction arrow.

Salicylic acid + Methanol ? catalyst Methyl salicylate + Water
Functional Group: _________ _________ _________

2. What are two uses of methyl salicylate?

3. Comment on the toxicity of methyl salicylate. What is considered a lethal dose, and what is its uptake avenue (inhalation, skin contact, ingestion, etc.)?

4. Why is the mixture reacted with a sodium bicarbonate solution? Write the reaction. It does NOT react with the limiting reagent since limiting reagents are completely consumed.

Part 2. Synthesis of an Ester.

Esters are compounds of the form RCOOR'. They occur naturally in many plants and animals, and can be synthesized. They have a pleasant aroma usually described as "fruity" or "flowery".

In a Fisher esterification, an ester is formed from the reaction of a carboxylic acid and an alcohol with a strong acid as a catalyst. The OH contained in the carboxylic acid group is replaced with the alkoxy group (O-R') from the alcohol, and an ester and water are formed.

O O
| ||
R—C—O—H + H—O—R' ? R—C—O—R' + H2O

Questions Oil of Wintergreen:

1. Draw the chemical reaction between salicylic acid (the limiting reagent) and methanol.
• Box the major functional group of each organic compound.
• Write the formula of the catalyst in the box above the reaction arrow.

Salicylic acid + Methanol ? catalyst Methyl salicylate + Water
Functional Group:

2. What are two uses of methyl salicylate?

3. Comment on the toxicity of methyl salicylate. What is considered a lethal dose, and what is its uptake avenue (inhalation, skin contact, ingestion, etc.)?

4. Why is the mixture reacted with a sodium bicarbonate solution? Write the reaction. It does NOT react with the limiting reagent since limiting reagents are completely consumed.

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