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Formula: HCOOH
Formula: CH3COOH
O H C OH
CARBOXYL GROUP
H O | H C C OH | H
Carboxyl group plays a vital role to gives acidic properties to carboxilic acid families. CH3COOH Ethanoic acid H+ + CH3COOHydrogen Ethanoate ion ion
Methanoic acid
O 46 H C OH
H O | 60 H C C OH | H
H C H Example 1: H H C H H C H H H C
H C H C
COOH
C4H8O2 / C3H7COOH
Example 2:
Attached alkyl group: 2-methyl
H CH3 C
COOH
Carboxyl carbon: carbon number 1
C2H5
Name: 2-methylbutanoic acid
C2H5
Ethanoic Asid Can be prepared through oxidation of an ethanol. Chemical equation: CH3CH2OH + 2[O] CH3COOH + H2O Etanol ethanoic acid
K2Cr2O7 solutions + dilute H2SO4 + 2[O] reflux
H H H C C OH H H
H O H C C OH + H O 2 H
This is carried out by refluxing ethanol with an oxidising agent such as acidified potassium dichromate(VI) or potassium manganate(VII) solution.
Wire gauge
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Heat
Condenser is used to prevent the loss of a volatile liquid by vaporisation. This method of retaining a volatile liquid during heating is called refluxing. How to carry out the activity?
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Physical Properties - pH less than 7 - sharp or unpleasant smell - turn moist blue litmus paper to red - colourless liquid Chemical Properties Acid Properties - Only hydrogen atom in the carboxyl group, [-COOH] can ionize in water to produce hydrogen ions, H+. CH3COOH Ethanoic acid CH3COO- + H+ CH3COOEthanoate Hydrogen ion ion
Ethanoic acid is a weak acid. Why? - it dissociates in water partially, most of the molecules remain unchanged.
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Reactions with metals - Dilute ethanoic acid reacts with reactive metal (Zn, Mg, Al) to produce a salt and hydrogen gas.
2CH3COOH + Mg Ethanoic acid Mg(CH3COO)2 + H2 Magnesium ethanoate
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Reactions with bases - Dilute ethanoic acid neutralizes alkalis such as sodium hydroxide solution to give an organic salt and water.
CH3COOH + NaOH CH3COONa + H2O Ethanoic acid Sodium ethanoate
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Reactions with carbonates - Dilute ethanoic acid reacts with metal carbonates to produce a salt, carbon dioxide and water.
2CH3COOH + Na2CO3 2CH3COONa + CO2 + H2O Ethanoic acid Sodium ethanoate
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Reactions with alcohols [Esterification] Esterification: Carboxilic acid reacts with alcohol to produce an ester and water.
Concentrated H2SO4 Carboxilic acid + Alcohol Ester + Water
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i. Ethanoic acid is known as acetic acids use in; - Food flavoring - Food preservatives - To make drugs, dyes, paints insectisides, plastics - To make esters for use as slovents ii. iii. iv. v. Methanoic acid is used to coagulate latex. Benzoic acids is used as food preservatives Fatty acids used in making soaps Carboxilic acids use in the manufactured of polyester and polyamids (fibres) in textile
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Conclusion on chemical reaction; Carboxilic acid + reactive metal carboxylate salt + hydrogen Carboxilic acid + base carboxylate salt + water Carboxylate acid + metal carbonate carboxylate salt + carbon dioxide + Water Carboxilic acid + alcohol ester + water 1. Learning task 2.9 Summarizing pg 75 [notes book] 2. Effective Practise pg 75 1, 2, 3 [exercise book]
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Esterification - Carboxilic acid reacts with alcohol to produce ester and water. - The functional group of ester is carboxilate group. - Concetrated sulphuric acid is catalyst. - Carboxilic acid losses OH and - Alcohol losses H - The bond that break up will rejoin again O CnH2n + 1 C
Derived from carboxilic acid Break up and rejoin
O
Carboxilate group, -COO-
CmH2m+1
Derived from alcohol
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Naming Ester - Name of ester consists of two parts, the name of alcohol part is given first and followed by the acid part. Example: i. Ethanoic acid + methanol methyl ethanoate + water Chemical equation:
CH3COOH + CH3OH CH3COOCH3 + H2O
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H | H C OH | H CH3OH (Methanol)
Water
Example: ii. Ethanoic acid + ethanol ethyl ethanoate + water Chemical equation:
CH3COOH + CH3CH2OH CH3COOCH2CH3 + H2O
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H O | H C C OH | H Ethanoic acid
H H | | H C C OH | | H H Ethanol
Example: iii. Methanoic acid + Ethanol ethyl methanoate + water Chemical equation:
HCOOH + CH3CH2OH HCOOCH2CH3 + H2O
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O H C OH Methanoic acid
H H | | H C C OH | | H H Ethanol
Q: Draw structural molecule of i. Methyl metanoate ii. Pentyl propanoate iii. Propyl ethanoate Solutions; i. Methyl metanoate
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Methyl methanoate
From carboxilic acid Methanoic acid O H C OH From alcohol Methanol H | H C OH | H Break up and rejoin O H | H C O C H + H2O | H methyl metanoate Air
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Prophyl ethanoate
From carboxilic acid Ethanoic acid H O | H C C OH | H From alcohol Propanol H H H | | | H C C C OH | | | H H H Break up and rejoin H O H H H | | | | H C C O C C C H + H2O | | | | H H H H propyl ethanoate Water
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Water bath
How to carry out this process? [Success pg 378] After boiling, Liebig condenser is rearranged To carry out the fractional distillation at 74oC 78oC to collect ethyl ethanoate.
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Physical properties of ethyl ethanoate - colourless - fragrant smell - insoluble in water - lese dense in water Natural Sources - Most simple esters are found in fruits and flowers. ex: benzyl ethanoate in Jasmine ethyl butanoate in pineapple
- Palm oil are liquid ester. - The higher and complex ester does not produce pleasant smells
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Uses of ester
- to make perfume, cosmetics - to make artificial food flavoring [Text Book: Table 2.8 pg 81] - used as organic solvents eg. ethyl ethanoate used in sunburn lotion, polish removers, glues. - to make synthetic polymers/fabrics - to make aspirin (pain reliever) Exercise: Effective Practise pg 84 no. 1-3 [Ex. Books]
Prepared by; Kamal Ariffin Bin Saaim SMKDBL http://kemhawk.webs.com
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