Carboxylic acids + Esters (P2+P3) Flashcards

1
Q

Describe the melting point and boiling point in carboxylic acids

A

they have hydrogen bonding so have high melting and boiling point.

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2
Q

The longer the carboxylic acid is the…

A

less soluble it is because the hydrocarbon chain is longer

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3
Q

How are esters formed?

A

carboxylic acid and alcohol
using H2SO4 catalyst
forming H2O as a by product
reaction is reversible.

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4
Q

What is Hydrolysis?

A

breaking a bond using water

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5
Q

What is acid catalysed hydrolysis?
equation for acid hydrolysis of propylethanoate

A

esters can be hydrolysed using a H+ catalyst.
CH3COOCH2CH2CH3 + H2O <–> CH3COOH + CH3CH2CH2OH

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6
Q

What is base catalysed hydrolysis?
equation for base hydrolysis of propylethanoate

A

esters can be hydrolysed using warm NaOH (base)
CH3COOCH2CH2CH3 + NaOH <–> CH3COONa + HOCH2CH2CH3
once the acid is formed it reacts with NaOH to form the salt.

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7
Q

How is a tri-ester formed?

A

an ester bond between propane-1,2,3-triol and 3 carboxylic acid chains.

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8
Q

General equation for acid hydrolysis of a tri-ester

A

tri-ester + 3H2O –> propane-1,2,3-triol + carboxylic acid
using an acid catalyst under reflux

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9
Q

General equation for base hydrolysis of a tri-ester

A

tri-ester + 3NaOH –> propane-1,2,3-triol + carboxylic acid salt (SOAP)

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10
Q

General equation to create biodiesel from fatty acids

A

fatty acids + 3CH3OH <–> 3HC-O-C=O-R + propane-1,2,3-triol

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11
Q

When an acyl chloride is reacted with water what functional group is formed?

A

Carboxylic acid

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12
Q

When an acyl chloride is reacted with an alcohol what functional group is formed?

A

Ester

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13
Q

When an acyl chloride is reacted with ammonia what functional group is formed?

A

Amide

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14
Q

When an acyl chloride is reacted with ammonia what functional group is formed?

A

Amide

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15
Q

When an acyl chloride is reacted with an amine what functional group is formed?

A

N-substituted Amide

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16
Q

Describe the mechanism for nucleophilic addition-elimination.

A

1st arrow from lone pair on nucleophile to C=O
2nd arrow from C=O onto O
structure of the intermediate
3rd arrow from O reforming the C=O bond
4th arrow from bond of C-Cl onto the Cl
5th arrow from Nu-H bond onto the Nu.