3.3.9- Carboxlyic Acids And Esters Flashcards
Basic structure of carboxylic acid
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Basic structure of ester
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What strength are carboxylic acids
Weak acids
What happens when carboxylic acid react with carbonates
Produce CO2
Show basic equation for making an ester
Carboxylic acid + alcohol – ester and water
Show the reaction to make ethyl propanoate
Propanoic acid + ethanol – ethyl propanoate + water
CH3CH2COOH + CH3CH2OH– CH3CH2COOCH2CH3
What are the conditions needed for esterfication
Strong acid catalyst -H2SO4
Uses of esters
Food flavourings
Solvents
Plasticisers
General structure of oils and fats
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What are oils /fats hydrolysed to
Form propan-1,2,3-triol
Which is glycerol and carboxylic acids
Draw the hydrolysis if oils/fats
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How do you make soap
Heat oil with concentrated sodium hydroxide produces glycerol and sodium salt of carboxylic acids
What are sodium salts
Soaps
Show equation to make soap
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Show equation to make biodiesel
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What is Acylation
The insertion of an Acyl group into a compound
What is the Acyl group
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Basic structure of acid anhydride
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Basic structure of Acyl chloride
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Basic structure of amides
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In nucleophilic addition elimination what are the products of Water Alcohols Ammonia Amines
Carboxylic acids
Esters
Amides
N-substituted amides
Draw the mechanism of Acyl chloride with water
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Draw the mechanism of Acyl chloride with alcohols
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Draw Acylation mechanism for Acyl chloride with amine
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Draw Acylation mechanism for Acyl chloride with ammonia
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What does a second mole of amine make in Acylation
RNH3+Cl-
What does a second mile of ammonia make in Acylation
Makes NH4+ Cl-
Draw Acylation mechanism for Acid anhydrides with water
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Draw Acylation mechanism for Acid anhydrides with alcohol
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Draw Acylation mechanism for Acid anhydrides with amine
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Draw Acylation mechanism for Acid anhydrides with ammonia
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What does second mole of amine make in Acylation with anhydrides
R1C=O
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O-N+H3R2
What does second mole of ammonia make in Acylation with acid anhydride
R1C=O
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O-NH4+
What is more useful in industry ethanoic anhydride or ethanoyl chloride
Ethanoic anhydride
Why is ethanoic anhydride more useful than ethanoyl chloride in industry
Cheaper
Less corrosive
Less vulnerable to hydrolysis
Less dangerous reaction
What is ethanoic anhydride and ethanoyl chloride used to make
Fibres
Aspirin
Why is ethanoyl chloride more useful in laboratory’s thank ethanoic anhydride
More reactive
Cleaner product and reaction
What does benzene look like
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Molecular formula of benzene
C6H6
Structure of benzene
Planar
Bond length of benzene
Intermediate between single and double
Explain the bonds in benzene
Each C bonded to 2 other C and 1 H so 1 unused electron
Unused electron is perpendicular to plane in p orbital
P orbitals overlap to form pi bonds negative charge above and below
What makes benzene even more stable
The electrons are delocalised so travel through whole system repelling each other making extra stable
What was the proposed structure of benzene and what would it be called
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Triene
Evidence against triene
1)C-C bond length
All the bonds are same length on triene there not 2) addition reactions
Benzene does not readily undergo these reactions (de colourising bromine water ) where as triene would
3) enthalpy of hydrogenation
Expect triene to react with 3H2 to form cyclohexane releasing 360KJ/mol(3x120) it only release 208 showing benzene is 152 more stable than triene extra stability because is delocalised electrons
What is extra stability called in benzene
Delocalisation stability
What is aromatic ring attacked by and why
Electrophile because is very electron rich
What reaction does and dosent benzene go through and why
Does go through substitution because h atom replaced but not addition as would lose delocalisation and extra stability
Reagents and conditions needed for nitration
Conc HNO3 and conc H2SO4
50C
Nitration generation of electrophile
HNO3+ H2SO4– NO2+ + 2HSo4- +H3O+
Nitration mechanism
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Regeneration of catalyst
H++ HSO4- — H2SO4
Conditions for Friedel Crafts Acylation and why
Need alcl3 and anhydrous (water has lone pairs )
Generation of electrophile in acyl chloride mechanism
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Friedel Crafts Acylation Acyl chloride mechanism
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Friedel Crafts Acylation regeneration of catalyst Acyl chloride
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Friedel Crafts acid anhydride generation of electrophile
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Friedel Crafts acid anhydride mechanism
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Friedel Crafts acid anhydride regeneration of catalyst
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Importance of nitration
1) manufactures of explosives
2) production of aromatic amines by reduction armotic nitro compound use Sn and HCl