See here: chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(McMurry)/21%3A_Carboxylic_Acid_Derivatives-_Nucleophilic_Acyl_Substitution_Reactions/21.02%3A_Nucleophilic_Acyl_Substitution_Reactions
No. Acid chlorides are the most reactive carboxylic acid derivatives, whereas carboxylic acids themselves are less reactive than any of their derivatives (chlorides, anhydrides, esters, or amides). To convert a carboxylic acid into an acid chloride, simple reaction with hydrochloride acid is worthless. (one can convert an alcohol into an alkyl chloride by reaction with HCl, but it is not the best way to do it.) To convert a carboxylic acid into an acid chloride, one needs to react with thionyl chloride (SOCl₂). See here: th-cam.com/video/TQ3yu_L6408/w-d-xo.html Does that help?
Take the example of hydronium ion, H₃O+. Oxygen has six (6) valence electrons, each hydrogen has (1) electron, which would give nine (9) electrons if it were neutral. However, if one (1) electron is removed (to give a total of 8), the species has a +1 charge. We can also think of it as water (H₂O) bound to a hydrogen ion (H+). H+ has no electrons, so the combination (H₃O+) has just eight (8) electrons (satisfying the octet rule) and having a +1 charge. The H+ ion binds to oxygen through one of oxygen's two lone pairs, forming a coordinate covalent bond.
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01:44 Structure of acid chloride
02:46 Nucleophilic acyl substitution
05:22 Mechanism of hydrolysis of acid chloride
10:04 Hydrolysis of formyl chloride
11:37 Hydrolysis of acetyl chloride
13:06 Hydrolysis of propionyl chloride
14:17 Hydrolysis of butyrl chloride
15:54 Table 1
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What would the best nucleophile for a hydrolysis reaction with acid chloride be?
See here:
chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(McMurry)/21%3A_Carboxylic_Acid_Derivatives-_Nucleophilic_Acyl_Substitution_Reactions/21.02%3A_Nucleophilic_Acyl_Substitution_Reactions
@@lseinjr1 thank you!
Is this mechanism reversible?
No. Acid chlorides are the most reactive carboxylic acid derivatives, whereas carboxylic acids themselves are less reactive than any of their derivatives (chlorides, anhydrides, esters, or amides). To convert a carboxylic acid into an acid chloride, simple reaction with hydrochloride acid is worthless. (one can convert an alcohol into an alkyl chloride by reaction with HCl, but it is not the best way to do it.)
To convert a carboxylic acid into an acid chloride, one needs to react with thionyl chloride (SOCl₂). See here: th-cam.com/video/TQ3yu_L6408/w-d-xo.html
Does that help?
@@lseinjr1 yes it does, thank you
How is the oxygen positive in the intermediate? I thought an oxygen having 3 covalent would be negative cuz now it has 9 electrons. How??
Take the example of hydronium ion, H₃O+. Oxygen has six (6) valence electrons, each hydrogen has (1) electron, which would give nine (9) electrons if it were neutral. However, if one (1) electron is removed (to give a total of 8), the species has a +1 charge.
We can also think of it as water (H₂O) bound to a hydrogen ion (H+). H+ has no electrons, so the combination (H₃O+) has just eight (8) electrons (satisfying the octet rule) and having a +1 charge. The H+ ion binds to oxygen through one of oxygen's two lone pairs, forming a coordinate covalent bond.
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