3.3.9 CARBOXYLIC ACIDS AND DERIVATIVES
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1
carboxylic acid functional group?
-COOH carboxyl
made of carbonyl and hydroxyl group
made of carbonyl and hydroxyl group
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Reaction of carboxylic acids with carbonates?
Theyre weak acids so partially disocciate to form -COO$^-$ (called carboxylate ion) and H$^+$
Form salt,H20,CO2
Form salt,H20,CO2
3
Esterification?
React alcohol with carboxylic acids in presence of acid catalyst(H2SO4).
Forms ester with functional group -COO and H20
Forms ester with functional group -COO and H20
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Name scheme of esters?
First part from alcohol second part from carboxylic acid
eg if ethanol reacted with methanoic acid it forms Ethyl methanoate
eg if butanol reacted with 2-methylpropanoaic acid it formsButyl 2-methylpropanoate
eg if ethanol reacted with methanoic acid it forms Ethyl methanoate
eg if butanol reacted with 2-methylpropanoaic acid it formsButyl 2-methylpropanoate
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Uses of esters
- Perfumes and food flavouring (Some have nice smell)
- Solvents (polar)
- Plasticisers
- Solvents (polar)
- Plasticisers
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Ester hydrolysis?
Esters split via H20 and acid catalyst (acid hydrolysis) or use a base only (base hydrolysis)
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Acid hydrolysis?
Add H20 and use dilute strong acid catalyst under reflux
Forms carboxylic acid + alcohol to equilibrium
Forms carboxylic acid + alcohol to equilibrium
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Base hydrolysis
Add strong dilute base under reflux
Forms carboxylate ion + alcohol and goes to completion( no equilibrium)
Forms carboxylate ion + alcohol and goes to completion( no equilibrium)
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How to form fats and oils?
Glycerol(alcohol) with 3 fatty acids(carboxylic acids) which forms fats and oils (esters)
Glycerol is propane-1,2,3-triol
3 Fatty acids can be saturated or unsaturated(biology yoooooooooo)
Glycerol is propane-1,2,3-triol
3 Fatty acids can be saturated or unsaturated(biology yoooooooooo)
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Fats and oils? difference?
Oils = glycerol + 3 UNsaturated fatty acids so form liquid
Fats = glycerol + 3 SATurated fatty acids so form solid
Fats = glycerol + 3 SATurated fatty acids so form solid
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How to form soap
Animal fats/vegetable oils hydrolysed by heating with 3NaOH.
Forming glycerol(receives H) and soap(receives NaO sodium salt)
Forming glycerol(receives H) and soap(receives NaO sodium salt)
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How to form biodiesel?
Vegetable oils with 3 methanol and potassium hydroxide as catalyst.
Forms glycerol(receives H) and 3 methyl ester(receives CH3O and is biodiesel)
Forms glycerol(receives H) and 3 methyl ester(receives CH3O and is biodiesel)
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Acyl group?
Derived from a carboxylic acid
RCO-
R = H or alkyl group
RCO-
R = H or alkyl group
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How to name acyl chlorides?
main alkane chain + anoyl chloride
eg
ethanoyl chloride
eg
ethanoyl chloride
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How do you form acyl chlorides
React any carboxylic acid with sulfur dichloride oxide (SOCL2)
Reaction forms acyl chloride + SO2 + HCL
Reaction forms acyl chloride + SO2 + HCL
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how to name acid anhydrides
Take the carboxylic acid it was formed from remove the "acid" part and add anhydride
eg methanoic anhydride
eg methanoic anhydride
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Nucleophillic addition elimination reactions?
Nucleophile is added to carbon centre and last step hydrogen is removed
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What are the four reactants we react with acyl chlorides or acid anhydrides?
Water
Alcohol
Ammonia
Primary amine
Note- these are nucleophillic addition elimination reactions
Alcohol
Ammonia
Primary amine
Note- these are nucleophillic addition elimination reactions
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Acyl chloride + H20? Do mechanism also ethanoyl chloride
Carboxylic acid + HCL
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Acyl chloride + alcohol? Do mechanism of propanoyl chloride + methanol
Ester + HCL
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Acyl chloride + ammonia do mechanism of ethanoyl chloride
amide + ammonia chloride
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Acyl chloride + primary amine do mechanism of butanoyl chloride
N-substituted amide + HCL
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Acid anhydride + H20? (actually is hydrolysis)
2 Carboxylic acids
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Acid anhydride + alcohol
Ester + carboxylic acid
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acid anhydride + ammonia
Amide + carboxylic acid
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acid anhydride + primary amine
N- substitued amide + carboxylic acid