Sei sulla pagina 1di 27

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

Formula: HCOOH

Formula: CH3COOH

O H C OH
CARBOXYL GROUP

H O | H C C OH | H

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

Molecular and Structural Formula


n Name Molecular formula C0H2(0)+1COOH = HCOOH Mr Structural formula

Methanoic acid

O 46 H C OH

C1H2(1)+1COOH 1 Ethanoic acid = CH3COOH [C2H4O2]

H O | 60 H C C OH | H

H H O CH COOH | | Propanoic 2 2(2)+1 74 H C C C OH acid = C2H5COOH | | H H Butanoic acid


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

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

Example 3: H C2H5 C COOH


Name: 2-ethyl pentanoic acid

C3H7 Example 4: H C3H7 C COOH


Name: 2-ethyl pentanoic 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.

Preparation of ethanoic acid through refluxing


Tissel tube Water out Liebig condenser Retort stand Water in Rounded bottom flask Absolute ethanol, C2H5OH + Acidified potassium dichromate(VI), K2Cr2O7 solution Label the diagram please

Wire gauge

xxxxxxxxxxxxxx

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?
8

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.
9

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

2CH3COOH + Zn Ethanoic acid

Zn(CH3COO)2 + H2 Zink ethanoate

6CH3COOH + 2Al 2Al(CH3COO)3 + 3H2 Ethanoic acid Aluminium ethanoate

10

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

- Black copper(II) oxide powder dissolves in dilute ethanoic acid.


2CH3COOH + CuO Cu(CH3COO)2 + H2O Ethanoic acid Copper(II) ethanoate

11

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

2CH3COOH + CaCO3 Ca(CH3COO)2 + CO2 + H2O Ethanoic acid Calcium ethanoate

12

Reactions with alcohols [Esterification] Esterification: Carboxilic acid reacts with alcohol to produce an ester and water.
Concentrated H2SO4 Carboxilic acid + Alcohol Ester + Water

Concentrated H2SO4 : catalyst [will discuss more in next chapter]

13

Uses of carboxilic acid:

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
14

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]
15

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

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

17

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

18

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. Ethanoic acid + ethanol ethyl ethanoate + water Chemical equation:
CH3COOH + CH3CH2OH CH3COOCH2CH3 + H2O

19

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

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. Methyl metanoate ii. Pentyl propanoate iii. Propyl ethanoate Solutions; i. Methyl metanoate
21

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

ii. Pentyl propanoate Try now

22

23

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 Porcelain chip To prevent bumping and ensure smooth boiling
XXXXXXXXXXXXXXX

Liebig condenser Water in

To cold the ethanol and ethanoic acid

Water bath

Ethanol + ethanoic acid + concentrated sulphuric acid

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.

25

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
26

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
27