CARBOXILIC ACID General formula CnH2n+1COOH One hydrogen atom is replaced with functional group – COOH

Formula: HCOOH

Formula: CH3COOH

O ║ H — C — OH

H O | ║ H — C — C — OH | H

CARBOXYL GROUP

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Why families known as carboxylic ‘acid’

Carboxyl group plays a vital role to gives acidic properties to carboxilic acid families. CH3COOH Ethanoic acid H+ + CH3COOHydrogen Ethanoate ion ion

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Molecular and Structural Formula n Name Molecular formula C0H2(0)+1COOH = HCOOH Mr Structural formula 0 Methanoic acid O ║ 46 H — C — OH C1H2(1)+1COOH 1 Ethanoic acid = CH3COOH [C2H4O2] H O | ║ 60 H — C — C — OH | H 2 H H O CH COOH | | ║ Propanoic 2 2(2)+1 74 H — C — C — C — OH acid = C2H5COOH | | H H Butanoic acid 3 3 .

Naming carboxilic acids 3 2 Carbon number 1 H C H Example 1: H H C H H C H H H C H C H C O O H Longest continuous chains: propanoic acid COOH C4H8O2 / C3H7COOH Carboxyl carbon: carbon number 1 Attached alkyl group: 2-methyl Name: 2-methylpropanoic acid 4 .

Example 2: Attached alkyl group: 2-methyl H CH3 C Longest continuous chains: butanoic acid COOH Carboxyl carbon: carbon number 1 C2H5 Name: 2-methylbutanoic acid 5 .

Example 3: H C2H5 C COOH Name: 2-ethyl pentanoic acid C3H7 Example 4: H C3H7 C COOH Name: 2-ethyl pentanoic acid C2H5 6 .

Chemical equation: CH3CH2OH + 2[O] → CH3COOH + H2O Etanol ethanoic acid K2Cr2O7 solutions + dilute H2SO4 reflux H H │ │ H — C — C — OH + 2[O] │ H │ H H O │ ║ H — C — C — OH + H2O │ H This is carried out by refluxing ethanol with an oxidising agent such as acidified potassium dichromate(VI) or potassium manganate(VII) solution. 7 .Ethanoic Asid Can be prepared through oxidation of an ethanol.

How to carry out the activity? 8 . K2Cr2O7 solution Wire gauge xxxxxxxxxxxxxx Heat Condenser is used to prevent the loss of a volatile liquid by vaporisation.Preparation of ethanoic acid through refluxing Tissel tube Water out Liebig condenser Label the diagram please Retort stand Water in Rounded bottom flask Absolute ethanol. This method of retaining a volatile liquid during heating is called refluxing. C2H5OH + Acidified potassium dichromate(VI).

H+. Why? .Only hydrogen atom in the carboxyl group.colourless liquid Chemical Properties Acid Properties .Physical Properties . [-COOH] can ionize in water to produce hydrogen ions.sharp or unpleasant smell .it dissociates in water partially. most of the molecules remain unchanged. CH3COOH Ethanoic acid CH3COO.+ H+ CH3COOEthanoate Hydrogen ion ion Ethanoic acid is a weak acid. 9 .pH less than 7 .turn moist blue litmus paper to red .

Reactions with metals .Dilute ethanoic acid reacts with reactive metal (Zn. 2CH3COOH + Mg Ethanoic acid → Mg(CH3COO)2 + H2 Magnesium ethanoate 2CH3COOH + Zn → Ethanoic acid Zn(CH3COO)2 Zink ethanoate + H2 6CH3COOH + 2Al Ethanoic acid → 2Al(CH3COO)3 + 3H2 Aluminium ethanoate 10 . Mg. Al) to produce a salt and hydrogen gas.

Reactions with bases .Black copper(II) oxide powder dissolves in dilute ethanoic acid. 2CH3COOH + CuO → Cu(CH3COO)2 + H2O Ethanoic acid Copper(II) ethanoate 11 . CH3COOH + NaOH → CH3COONa + H2O Ethanoic acid Sodium ethanoate .Dilute ethanoic acid neutralizes alkalis such as sodium hydroxide solution to give an organic salt and water.

Reactions with carbonates . 2CH3COOH + Na2CO3 → 2CH3COONa + CO2 + H2O Ethanoic acid Sodium ethanoate 2CH3COOH + CaCO3 → Ca(CH3COO)2 + CO2 + H2O Ethanoic acid Calcium ethanoate 12 . carbon dioxide and water.Dilute ethanoic acid reacts with metal carbonates to produce a salt.

Concentrated H2SO4 Carboxilic acid + Alcohol ———→ Ester + Water Concentrated H2SO4 : catalyst [will discuss more in next chapter] 13 .Reactions with alcohols [Esterification] Esterification: Carboxilic acid reacts with alcohol to produce an ester and water.

plastics .Food flavoring . iv.To make drugs. paints insectisides. v. 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 14 . .To make esters for use as slovents ii. Ethanoic acid is known as acetic acids use in. dyes.Uses of carboxilic acid: i. Methanoic acid is used to coagulate latex. iii.Food preservatives .

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. Effective Practise pg 75 1. 2.Conclusion on chemical reaction.9 Summarizing pg 75 [notes book] 2. 3 [exercise book] 15 . Learning task 2.

ESTER General formula CnH2n+1COOCmH2m+1 R : alkyl group in carboxilic acid R’ : alkyl group in alcohol O ║ CnH2n + 1C — OH + CmH2m+1OH (carboxilic acid) (alcohol) O ║ CnH2n + 1C — O — CmH2m+1 + H2O (ESTER) 16 .

-COO- CmH2m+1 Derived from alcohol 17 . .Concetrated sulphuric acid is catalyst.The functional group of ester is carboxilate group.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.Carboxilic acid reacts with alcohol to produce ester and water.Esterification . .Carboxilic acid losses ‘OH’ and . .

Naming Ester . Example: i. Ethanoic acid + methanol  methyl ethanoate + water Chemical equation: CH3COOH + CH3OH → CH3COOCH3 + H2O 18 .Name of ester consists of two parts. the name of alcohol part is given first and followed by the acid part.

Ethanoic acid + ethanol  ethyl ethanoate + water Chemical equation: CH3COOH + CH3CH2OH → CH3COOCH2CH3 + H2O 19 .H O | ║ H — C — C — OH | H CH3COOH (Etanoic acid) + H | H— C — OH | H CH3OH (Methanol) H O H | ║ | H — C — C — O — C — H + H2O | | H H CH3COOCH3 (Methyl ethanoat) Water Example: ii.

H O | ║ H — C — C — OH | H Ethanoic acid + H H | | H— C — C — OH | | H H Ethanol H O H H | ║ | | H — C — C — O — C — C — H + H2O | | | H H H ethyl etanoat Water Example: iii. Methanoic acid + Ethanol  ethyl methanoate + water Chemical equation: HCOOH + CH3CH2OH → HCOOCH2CH3 + H2O 20 .

Methyl metanoate ii.O ║ H — C — OH Methanoic acid + H H | | H— C — C — OH | | H H Ethanol O H H ║ | | H — C — O — C — C — H + H2O | | H H Ethyl metanoat Air Q: Draw structural molecule of i. Pentyl propanoate iii. i. Methyl metanoate 21 . Propyl ethanoate Solutions.

Pentyl propanoate Try now methyl metanoate Air 22 .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 ii.

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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 24 .

Preparation of ester through reflux Tissel tube Water out Uniform heating Water bath Liebig condenser Water in To cold the ethanol and ethanoic acid Porcelain chip To prevent bumping and ensure smooth boiling XXXXXXXXXXXXXXX Ethanol + ethanoic acid + concentrated sulphuric acid How to carry out this process? [Success pg 378] After boiling. 25 . Liebig condenser is rearranged To carry out the fractional distillation at 74oC – 78oC to collect ethyl ethanoate.

fragrant smell .The higher and complex ester does not produce pleasant smells 26 .colourless . ex: benzyl ethanoate in Jasmine ethyl butanoate in pineapple . .Most simple esters are found in fruits and flowers.Physical properties of ethyl ethanoate .lese dense in water Natural Sources .insoluble in water .Palm oil are liquid ester.

Books] Prepared by.Uses of ester . ethyl ethanoate used in sunburn lotion.webs.com 27 . .to make aspirin (pain reliever) Exercise: Effective Practise pg 84 no. polish removers.8 pg 81] . 1-3 [Ex.to make artificial food flavoring [Text Book: Table 2. cosmetics . Kamal Ariffin Bin Saaim SMKDBL http://kemhawk.used as organic solvents eg.to make synthetic polymers/fabrics .to make perfume. glues.

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