Carboxylic Acid Derivatives DAT
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37 Terms
Reactivity trend for carboxylic acid derivatives
acid chloride > acid anhydride > carboxylic acids/esters > amides > carboxylates
carboxylic acid + SOCl2 ————>
acid chloride
acid chloride + OH- ————>
carboxylate
carboxylate + H+ ————>
carboxylic acid
acid chloride + R==O—OH (carboxylic acid) ————>
acid anhydride
acid chloride + R==O—O^- (carboxylate) ————>
acid anhydride
acid chloride + ROH or RO^- ————>
ester
acid chloride + R2NH or R2N ————>
amide
amide + H3O/Heat ————>
carboxylic acid
carboxylic acid + NR2/Heat ————>
amide
RMgX + CO2 ————>
Carboxylic acid formation from Grignard reagent
Carboxylic acid + R’OH, H+ ————>
Ester formation (fischer esterification)
ester + H2O, H+ ————>
carboxylic acid formation (saponification/hydrolysis)
ester + OH^- + H+ ————>
Carboxylic acid formation (saponification, basic conditions)
What molecules is NaBH4 able to reduce?
NaBH4 can reduce aldehydes, ketones, acid chlorides and acid anhydrides to alcohols
What molecules can LiAlH4 reduce?
LiAlH4 can reduce aldehydes, ketones, acid chlorides, acid anhydrides, esters, amides, AND carboxylic acids to alcohols
amide + LiAlH4 ————>
Amine formation
amide + LiAlH4 ————>
amine (1 Carbon bond shorter)
ester + DIBAL-H ————>
Aldehyde formation
acid chloride + LTBA ————>
Aldehyde formation
amide + LiAlH4 ————>
Amine formation
Nitrile + LiAlH4 ————>
1* amine formation
How do esters react with gringard reagents?
Gringard reagents are strong R^- groups, the R^- group gets added 2 times into the ester C==O bond and forms a 3* alcohol
ester + RMgX ————>
3* alcohol formation
How do acid chlorides react with gringard reagents?
Gringard reagents are strong R^- groups, the R^- group gets added 2 times into the C==O bond and forms a 3* alcohol
acid chloride + RMgX ————>
3* alcohol
how do carboxylic acids react with gringard reagents?
Since carboxylic acids have H+ groups, the gringard R- will just form a deprotonated carboxylate
carboxylic acid + RMgX ————>
amide + GMgX ————>
deprotonated amide
nitrile + RMgX ————>
Ketone formation
Nitrile + H3O+ ————>
Carboxylic acid formation (nitrile hydrolysis)
