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How would you synthesize 4-Propyl-4-heptanol starting from ethyl butanoate using a Grignard reaction?

1. What Grignard reagent is needed?
2. What does the complete mechanism look like?

Answer :

Final answer:

To synthesize 4-Propyl-4-heptanol starting from ethyl butanoate using a Grignard reaction, you need to react ethyl butanoate with magnesium metal in anhydrous ether to prepare the Grignard reagent. Then, react the Grignard reagent with a carbonyl compound containing the desired alcohol functional group. The complete mechanism involves the formation of a new carbon-carbon bond and the addition of a proton to form the alcohol.

Explanation:

To synthesize 4-Propyl-4-heptanol starting from ethyl butanoate using a Grignard reaction, we need to follow a step-by-step process:

  1. Prepare the Grignard reagent: To do this, we react ethyl butanoate with magnesium metal in anhydrous ether. The reaction can be represented as follows:
    ethyl butanoate + magnesium metal → Grignard reagent
  2. React the Grignard reagent with a carbonyl compound: In this case, we react the Grignard reagent with a carbonyl compound that contains the desired alcohol functional group. The reaction can be represented as follows:
    Grignard reagent + carbonyl compound → alcohol
  3. Isolate and purify the product: After the reaction, the product, 4-Propyl-4-heptanol, can be isolated and purified using standard laboratory techniques.

The complete mechanism of the Grignard reaction involves the formation of a new carbon-carbon bond between the Grignard reagent and the carbonyl compound. This is followed by the addition of a proton to the resulting intermediate, resulting in the formation of the alcohol.

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