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24 Cards in this Set
- Front
- Back
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What is a carboxyl group?
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It is fundamentally a carbonyl group. The difference is that this carbonyl group has an OH group attached to it.
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Naming Carboxylic Acids
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When you see a carboxylic acid, count the number of carbons and add the suffix -oic acid to end of the name.
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Priority of Carboxylic acid
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The carboxyl group has a very high priority so when you are number the carbon chain, you need to give this functional group the lowest possible number
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2 to7 carbon chain dicarboxylic acid
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oxalic, malonic, succinic, glutaric,adipic, pimelic
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Why do cacboxylic acids have such high boiling points?
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Given the fact they they that there are two points on the molecule that can participate in hydrogen bonding the bonding is much stronger
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What is a carboxylate anion?
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The conjugate base of the carboxylic acid. It is simply the carboxylic acid with the H removed from the hydroxy group.
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Why is the carboxylic acid such a strong acid?
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Because when the H from the hydroxyl group dissociates, the negative charge is very well stabilized by the two oxygen molecules
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How does the stability of the negative charge on the conjugate base of what was an acid affect the overall acidity of the molecule?
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The better able a molecule is able to stabilize a negative charge the stronger acid it is.
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Impact of electron withdrawing/electron donating groups.
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The better able a molecule is stabilizing a negative charge, the stronger acid it will be. As such, if you have an electron withdrawing group it will 'suck up' the electrons making the molecule better at dealing and spreading out the negative charge. However, if you have a molecule that give electrons, it will destabilize the the molecule by adding more negative charge.
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Two ways to stabilize a negative charge on a molecule?
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1) Adding electron withdrawing groups
2) Increasing resonance |
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Cl and NO2 are examples of what.
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Electron withdrawing groups
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NH2 and OCH3 are example of what
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Electron donating groups
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What happens if you have a dicarboxlyic acid and one of the carboxyl groups loses it proton
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Dicarboxylic acid groups are generally more acidic but if a proton is lost from one of them, then the other carboxyl group becomes less acidic. The reason being that when the H leaves the carboxyl group, it ends up leaving a NEGATIVE oxygen molecule which adds negative charge thus making the molecule less acidic
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Alcohol + KMnO4
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This is classic. It will give you a carboxylic acid. `
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Making a carboxylic acid with a gringard reagent
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Alkyl Halide --- Treat with Mg/Ether -- You will end up with alkane with MgBr on the end (the Mg just adds to the Br) -- Treat with CO2 gas/H+, H2O--Carboxylic acid results
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Making a carboxylic acid with cyanide
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Alkly Halide + cyanide -- Cyanide will displace the halide ion and attach to the alkyl group -- Treat with H+/H20 -- result will be ammonium and a carboxylic acid
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Reaction between long chain carboxylic acids and Na or KOH
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They will form a salt in which the Na will displace the H on the hydroxyl group and form a salt. This is useful in the formation of soap which form micelles around polar molecule
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Nucleophillic Acyl Substitution
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A nucleophile will attack the carbon on the carbonyl group and the will displace the hydroxyl group which is the leaving group
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Carboxylic Acid + LAH
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LAH will reduce the carboxylic acid to an alcohol
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What is an ester?
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It is a hybrid between carboxylic acid and an ether
http://www.chemistry-drills.com/icons/4.JPG |
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Carboxylic Acid + Alcohol
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Will form an ester. Lone pairs on the alcohol will attack the nucleophilic carbon on the carboxylic acid. The hydroxyl group on the carboxylic acid will get protonated (becoming water) and dissociate.
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Carboxylic Acid + SOCl2 (Thionyl Chloride)
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Will form an acyl halide which is a carbonyl group that has a halide attached to it
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If a carbon is lost in reaction, how will it be given off?
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As CO2 gas
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How would you decarboxylate a carboxylic acid?
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By heating it.
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