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Mechanism for oxidative cleavage of tertiary alcohols by NaOCl
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Kevin Counihan
Mechanism for oxidative cleavage of tertiary alcohols by NaOCl
Reaction of an ester with a Grignard reagent gives two products: (1) a tertiary alcohol coming from the carbonyl carbon and two equivalents of the Grignard reagent and (2) an alcohol liberated from the ester. I believe it's this liberated alcohol that is reacting with bleach, since a tertiary alcohol is typically resistant to oxidation. However, the liberated alcohol might be primary, secondary, or tertiary depending on the identity of R2.
The information given says that after treatment with bleach, acetic acid is formed. This tells us two things: (1) that liberated alcohol is a primary alcohol, since the oxidation goes all the way to an acid and (2) that liberated alcohol has two carbons, since acetic acid has two carbons. That implies that the liberated alcohol is ethanol. The starting ester has four carbons total, which leaves two carbons for the carboxy fragment. The original ester was ethyl acetate.
Reaction of an ester with a Grignard reagent gives two products: (1) a tertiary alcohol coming from the carbonyl carbon and two equivalents of the Grignard reagent and (2) an alcohol liberated from the ester. I believe it's this liberated alcohol that is reacting with bleach, since a tertiary alcohol is typically resistant to oxidation. However, the liberated alcohol might be primary, secondary, or tertiary depending on the identity of R2.
The information given says that after treatment with bleach, acetic acid is formed. This tells us two things: (1) that liberated alcohol is a primary alcohol, since the oxidation goes all the way to an acid and (2) that liberated alcohol has two carbons, since acetic acid has two carbons. That implies that the liberated alcohol is ethanol. The starting ester has four carbons total, which leaves two carbons for the carboxy fragment. The original ester was ethyl acetate.
Reaction of an ester with a Grignard reagent gives two products: (1) a tertiary alcohol coming from the carbonyl carbon and two equivalents of the Grignard reagent and (2) an alcohol liberated from the ester. I believe it's this liberated alcohol that is reacting with bleach, since a tertiary alcohol is typically resistant to oxidation. However, the liberated alcohol might be primary, secondary, or tertiary depending on the identity of R2.
The information given says that after treatment with bleach, acetic acid is formed. This tells us two things: (1) that liberated alcohol is a primary alcohol, since the oxidation goes all the way to an acid and (2) that liberated alcohol has two carbons, since acetic acid has two carbons. That implies that the liberated alcohol is ethanol. The starting ester has four carbons total, which leaves two carbons for the carboxy fragment. The original ester was ethyl acetate.
Reaction of an ester with a Grignard reagent gives two products: (1) a tertiary alcohol coming from the carbonyl carbon and two equivalents of the Grignard reagent and (2) an alcohol liberated from the ester. I believe it's this liberated alcohol that is reacting with bleach, since a tertiary alcohol is typically resistant to oxidation. However, the liberated alcohol might be primary, secondary, or tertiary depending on the identity of R2.
The information given says that after treatment with bleach, acetic acid is formed. This tells us two things: (1) that liberated alcohol is a primary alcohol, since the oxidation goes all the way to an acid and (2) that liberated alcohol has two carbons, since acetic acid has two carbons. That implies that the liberated alcohol is ethanol. The starting ester has four carbons total, which leaves two carbons for the carboxy fragment. The original ester was ethyl acetate.
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