Grignard reaction product involving a ketone

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SUMMARY

The discussion centers on the Grignard reaction involving a ketone, specifically the conversion of a ketone to an alcohol. The participant initially proposed that the product was 3-phenyl-3-pentanol, but later sought clarification on why the reaction yielded an alkene instead of the expected alcohol. The key to understanding this discrepancy lies in the dehydration step facilitated by sulfuric acid (H2SO4), which acts as a dehydrating agent, leading to the formation of an alkene.

PREREQUISITES
  • Understanding of Grignard reaction mechanisms
  • Knowledge of ketone and alcohol functional groups
  • Familiarity with dehydration reactions
  • Basic chemistry of sulfuric acid as a dehydrating agent
NEXT STEPS
  • Study the detailed mechanism of the Grignard reaction
  • Learn about dehydration reactions and their conditions
  • Investigate the role of sulfuric acid in organic synthesis
  • Explore the properties and reactions of alkenes
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Chemistry students, organic chemists, and anyone studying reaction mechanisms involving Grignard reagents and ketones.

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Homework Statement



Basically I have to show the product of this reaction:

Question.PNG




Homework Equations



Grignard reaction mechanism:
The conversion of a ketone to an alcohol

The Attempt at a Solution



My attempt of this reaction produces an alcohol with two ethyl groups attached to the central carbon as well as a phenyl group and an OH group attached to the central carbon, so the IUPAC name would be 3-phenyl-3-pentanol.

However, the answer is:
answer.PNG


Can someone please explain why the reaction produced an alkene instead of an alcohol. I do not know why this occurred and need some clarification. Also, when does this extra step occur.

Thanks.
 
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Think a little about step 3.
 
What occurs is step 3? I know that the H2SO4 is deprotonated to become HSO4. This produces the alcohol part of the compound, which is what I got. I am going to assume that deprotonation of HSO4 occurs, thus producing water and the alkene as shown in the answer. Is this right?
 
Look up "dehydration". Sulfuric acid is a powerful dessicant.
 

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