Addition of Grignard reagents to esters to give tertiary alcohols
Description: Grignard reagents add twice to esters, giving tertiary alcohols (after addition of acid)
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Real-World Examples:
Org. Synth. 1926, 6, 32
DOI Link: 10.15227/orgsyn.006.0032
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Org. Synth. 1944, 24, 41
DOI Link: 10.15227/orgsyn.024.0041
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Org. Synth. 1943, 23, 98
DOI Link: 10.15227/orgsyn.023.0098
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Org. Synth. 1958, 38, 41
DOI Link: 10.15227/orgsyn.038.0041
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In the third example shouldn’t the diol go through dehydration and become a cyclic ether
Yeah, I think you are right. The product can form stable carbocation in the more substituted carbon and then cyclic reaction.
Good point. Instructors differ on how to handle the quench step. To some, H+ is “too harsh”, resulting in precisely the result you describe. To others, “H+” is fine. I should have written, “mild acid”.