This document provides information about carboxylic acids for organic chemistry students. It defines carboxylic acids and discusses their structures, naming conventions, physical properties, acidity, and common reactions. Specifically, it describes how carboxylic acids ionize in water, the effect of substituents on acidity, substitution reactions of benzoic acids, and reactions such as esterification, halogenation, and amide formation. Examples of dicarboxylic acids and aromatic derivatives are also provided. The document aims to explain key concepts and properties of carboxylic acids to help students learn organic chemistry.
Teori orbital molekul merupakan teori yang paling lengkap karena menyangkut interaksi elektrostatik dan interaksi kovalen . Berdasarkan teori orbital molekul, pada pembentukkan senyawa kompleks, orbital-orbital pada atom pusat dengan orbital-orbital dari ligan saling berinteraksi membentuk orbital-orbital molekul baru. Berdasarkan pedekatan linier, orbital-orbital molekul senyawa kompleks dianggap merupakan kombinasi linier dari orbital-orbital atom pusat dan orbital-orbital ligan. Perbedaan energy antara orbital-orbital atom pusat dengan ligan dapat diabaikan oleh karena itu dalam menggambarkan orbital molekul senyawa kompleks cukup digambarkan dengan orbital-orbital valensinya
Aldehid dan keton adalah keluarga besar dari senyawa organik yang merasuk dalam kehidupan sehari- hari kita. Senyawa-senyawa ini menimbulkan bau wangi pada banyak buah-buahan dan parfum mahal.Senyawa aldehida dan keton yaitu atom karbon yang dihubungkan dengan atom oksigen oleh ikatan ganda dua (gugus karbonil). Aldehida adalah senyawa organik yang karbon-karbonilnya (karbon yang terikat pada oksigen) selalu berikatan dengan paling sedikit satu hydrogen
Teori orbital molekul merupakan teori yang paling lengkap karena menyangkut interaksi elektrostatik dan interaksi kovalen . Berdasarkan teori orbital molekul, pada pembentukkan senyawa kompleks, orbital-orbital pada atom pusat dengan orbital-orbital dari ligan saling berinteraksi membentuk orbital-orbital molekul baru. Berdasarkan pedekatan linier, orbital-orbital molekul senyawa kompleks dianggap merupakan kombinasi linier dari orbital-orbital atom pusat dan orbital-orbital ligan. Perbedaan energy antara orbital-orbital atom pusat dengan ligan dapat diabaikan oleh karena itu dalam menggambarkan orbital molekul senyawa kompleks cukup digambarkan dengan orbital-orbital valensinya
Aldehid dan keton adalah keluarga besar dari senyawa organik yang merasuk dalam kehidupan sehari- hari kita. Senyawa-senyawa ini menimbulkan bau wangi pada banyak buah-buahan dan parfum mahal.Senyawa aldehida dan keton yaitu atom karbon yang dihubungkan dengan atom oksigen oleh ikatan ganda dua (gugus karbonil). Aldehida adalah senyawa organik yang karbon-karbonilnya (karbon yang terikat pada oksigen) selalu berikatan dengan paling sedikit satu hydrogen
Asam organik adalah suatu senyawa yang mengandung gugusan karboksil, suatu istilah yang berasal dari karbonil dan hidroksil.
Gugusan yang terikat pada gugusan karboksil dalam asam karboksilat bisa gugus apa saja, bahkan bisa gugus karboksil lain.
Dalam asam karboksilat gugus -COOH terikat pada gugus alkil (-R) atau gugus aril (-Ar). Meskipun yang mengikat gugus –COOH dapat berupa gugus alifatik atau aromatic, jenuh atau tidak jenuh, tersubstitusi atau tidak tersubstitusi sifat yang diperlihatkan oleh gugus –COOH tersebut pada dasarnya sama.
Di samping terdapat asam yang mengandung satu gugus karboksil (asam monokarboksilat), diketahui juga terdapat asam yang memiliki dua gugus karboksil (asam dikarboksilat) dan tiga buah gugus karboksil (asam trikarboksilat).
Perbedaan banyaknya gugus –COOH ini tidak mengakibatkan perubahan sifat kimia yang mendasar.
The combination of a carbonyl group and a hydroxyl on the same carbon atom is called a carboxyl group. Compounds containing the carboxyl group are called carboxylic acids. The carboxyl group is one of the most widely occurring functional groups in organic chemistry.
Aromatic Carboxylic acids: Carboxylic acids have an aryl group bound to the carboxyl group is known as aromatic carboxylic acids. The general formula of an aliphatic aromatic carboxylic acid is Ar-COOH.
Acidity of carboxylic acid:
A carboxylic acid may dissociate in water to give a proton and a carboxylate ion. Dissociation of a carboxylic acid involves breaking an O-H bond gives a carboxylate ion with the negative charge spread out equally over two oxygen atoms, compared with just one oxygen atom in an alkoxide ion. The delocalized charge makes the carboxylate ion more stable therefore; dissociation of a carboxylic acid to a carboxylate ion is less endothermic.
Preparation Methods:
1. Oxidation:
The oxidation of aldehyde with oxidizing agents such as CrO3 to forms carboxylic acids containing the same numbers of carbon atoms with a oxidizing agents like chromic acid, chromium trioxide. The silver oxide (Ag2O) in aqueous ammonia solution (Tollen’s reagent) is mild reagent give good yield at room temperature. E.g. Acetaldehyde reacts with CrO3 in aqueous acid to give acetic acid.
2. Grignard reagents (from CO2):
Carboxylic acid can be prepared by the reaction of Grignard reagent (alkyl magnesium halide) with carbon dioxide (CO2) in presence of dry ether. Grignard reagents react with carbon dioxide to forms a magnesium carboxylates which on hydrolysis by dilute HCl produces carboxylic acids.
3. Hydrolysis of nitrile:
The hydrolysis of nitrile or cyanide in presence of dilute acid to forms a carboxylic acid. In this reaction –CN group is converted to a –COOH group.
4. Hydrolysis Reactions:
All the carboxylic acid derivatives can be hydrolyzed into the carboxylic acid in the acidic or basic media; the hydrolysis reaction is fast and occurs in presence of water with no acid or base catalyst.
1. From Ester (Hydrolysis of ester): Ester can be hydrolyzed in either acidic or basic medium to yield carboxylic acid. The ester is heated with an excess of water contains strong acid or base catalyst.
Properties of Carboxylic Acids:
1. Low molecular weights carboxylic acids are colourless liquid at room temperature i.e. lower member ate liquid up to C9 and have characteristic odors whereas higher members are solid.
2. Carboxylic acids are polar organic compound. Low molecular weight carboxylic acids (first four members) are soluble in water whereas solubility in water decrease as molecular weight and chain lengthing increases.
3. Aromatic acids are insoluble in water.
4. Carboxylic acids have higher melting and boiling point due to their capacity to readily form stable hydrogen-bonded dimers.
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http://sandymillin.wordpress.com/iateflwebinar2024
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Prepare a presentation or a paper using research, basic comparative analysis, data organization and application of economic information. You will make an informed assessment of an economic climate outside of the United States to accomplish an entertainment industry objective.
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2. Mahasiswa dapat:
Menggambarkan struktur asam karboksilat,
memberi nama asam karboksilat,
menjelaskan sifat keasaman
Menjelaskan konsep penarik dan pendorong elektron
Menjelaskan efek orto pada asam karboksilat
aromatik, menjelaskan sifat-sifat fisika asam
karboksilat.
Menuliskan reaksi-reaksi pembuatan asam
karboksilat
Menuliskan reaksi-reaksi asam karboksilat
Menuliskan rumus umum asam dikarboksilat
Menyebutkan sifat-sifat asam dikarboksilat
3. Organic Chemistry, 7th edition, John
McMurry
Organic Chemistry, T. W. Graham
Solomons
Organic Chemistry, Fessenden and
Fessenden
4.
5. A general acyl group (blue) as an acylium ion (top centre), as an
acyl radical (top right), in a ketone (top left), an aldehyde (bottom
left), ester (bottom centre) or amide (bottom right). (R1, R2, R3 =
organyl substituents or hydrogen).
6. Structure and Bonding
• Carboxylic acids are compounds containing a carboxy
group (COOH).
• The structure of carboxylic acids is often abbreviated
as RCOOH or RCO2H, but keep in mind that the central
carbon atom of the functional group is doubly bonded
to one oxygen atom and singly bonded to another.
7. The two most important features of the carbonyl group are:
·Because oxygen is more electronegative than either carbon or hydrogen,
the C—O and O—H bonds are polar.
8. Carboxylic Acids, R-COOH
If derived from open-chain alkanes, replace the
terminal -e of the alkane name with -oic acid
The carboxyl carbon atom is C1
Common names: IUPAC Common
HCO2H methanoic acid formic acid
CH3CO2H ethanoic acid acetic acid
CH3CH2CO2H propanoic acid propionic acid
CH3CH2CH2CO2H butanoic acid butyric acid
CH3CH2CH2CH2CO2H pentanoic valeric acid
8
9. 5 4 3 2 1
C — C — C — C — C = O
δ γ β α used in common names
11. Compounds with CO2H bonded to a ring are named
using the suffix -carboxylic acid
The CO2H carbon is not itself numbered in this
system
Use common names for formic acid (HCOOH) and
acetic acid (CH3COOH)
11
13. salts of carboxylic acids:
name of cation + name of acid: drop –ic acid, add –ate
CH3CO2Na sodium acetate or sodium ethanoate
CH3CH2CH2CO2NH4 ammonium butyrate
ammonium butanoate
(CH3CH2COO)2Mg magnesium propionate
magnesium propanoate
14.
15. Carboxylic acids transfer a proton to water to give
H3O+ and carboxylate anions, RCO2
15
, but H3O+ is a
much stronger acid
The acidity constant, Ka,, is about 10-5 for a typical
carboxylic acid (pKa ~ 5)
16. Fluoroacetic, chloroacetic, bromoacetic, and
iodoacetic acids are stronger acids than acetic acid
Multiple electronegative substituents have
synergistic effects on acidity
17
17. If pKa of given acid and the pH of the medium
are known, % of dissociated and undissociated
forms can be calculated using the Henderson-
Hasselbalch eqn
18
20. Substituted Benzoic Acids
Recall that substituents on a benzene ring either donate or
withdraw electron density, depending on the balance of their
inductive and resonance effects. These same effects also
determine the acidity of substituted benzoic acids.
[1] Electron-donor groups destabilize a conjugate base, making
an acid less acidic—The conjugate base is destabilized
because electron density is being donated to a negatively
charged carboxylate anion.
21
21. [2] Electron-withdrawing groups stabilize a conjugate base, making an
acid more acidic. The conjugate base is stabilized because
electron density is removed from the negatively charged
carboxylate anion.
22
22. 23
Figure 19.8
How common substituents
affect the reactivity of a
benzene ring towards
electrophiles and the acidity of
substituted benzoic acids
23. Subtituen posisi orto dari turunan asam benzoat selalu
meningkatkan sifat keasaman senyawa tersebut karena
subtituen ini mengurangi resonansi luar cincin.
Efek orto pada asam benzoat tidak tergantung pada jenis
substituen apakah cenderung menarik atau melepaskan
elektron.
Efek resonansi sangat berpengaruh terhadap kekuatan
asam. Subtituen yang berada pada posisi orto akan
mengurangi resonansi luar cincin sehingga akan
meningkatkan kekuatan asam.
Senyawa turunan asam benzoat yang mempunyai
kekuatan asam tertinggi adalah senyawa turunan asam
benzoate yang subtituennya terletak pada posisi orto.
24. 1. Wujud
Pada temperatur kamar, asam karboksilat yang bersuku rendah
adalah zat cair yang encer, suku tengah berupa zat cair yang
kental, dan suku tinggi berupa zat padat yang tidak larut dalam
air.
Rumus Struktur T d
H-COOH 101
CH3-COOH 118
CH3-CH2-COOH 141
CH3-CH2-CH2-COOH 163
CH3-CH2-CH2-CH2-COOH 187
2. Titik didih dan titik leleh
Asam karboksilat membentuk ikatan
hidrogen berupa siklik dimer
antarmolekul. Ikatan hidrogen yang kuat
ini menyebabkan TD dan TL lebih tinggi
dari alkohol yang bersesuaian.
25. 3. Kelarutan
Carboxylic acids are proton donors toward weak and strong
bases, producing metal carboxylate salts, RCO + M
2
Carboxylic acids with more than six carbons are only slightly
soluble in water, but their conjugate base salts are water-soluble
4. Daya hantar listrik
Asam karboksilat dapat terionisasi sebagian dalam air,
sehingga termasuk senyawa elektrolit lemah.
R-COOH ⇋ R-COO- + H+
28. 1. Reaksi dengan Basa (penyabunan)
R-COOH + NaOH → R-COONa + H2O
2. Reaksi esterifikasi
sabun
H2SO4
R-COOH + R’-OH → R-COOR’ + H2O
Asam karboksilat Alkohol Ester
3. Reaksi dengan PCl5
R-COOH + PCl5 → R-CO-Cl + POCl3 + HCl
Alkanoilklorida
4. Reaksi dengan NH3
R-COOH + NH3 → R-CONH2 + H2O
Amida
5. Reaksi dengan Cl2
CH3-CH2-COOH + Cl2 → R-CHCl-COOH + HCl
Asam 2-monokloropropanoat
29. Reactions of Carboxylic Acids
The most important reactive feature of a carboxylic acid is its polar O—H
bond, which is readily cleaved with base.
30. • The nonbonded electron pairs on oxygen create electron-rich
sites that can be protonated by strong acids (H—A).
• Protonation occurs at the carbonyl oxygen because the resulting
conjugate acid is resonance stabilized (Possibility [1]).
• The product of protonation at the OH group (Possibility [2])
cannot be resonance stabilized.
31. • The polar C—O bonds make the carboxy carbon electrophilic. Thus,
carboxylic acids react with nucleophiles.
• Nucleophilic attack occurs at an sp2 hybridized carbon atom, so it
results in the cleavage of the bond as well.
32. Carboxylic Acids—Strong Organic BrØnsted-Lowry Acids
• Carboxylic acids are strong organic acids, and as such, readily react
with BrØnsted-Lowry bases to form carboxylate anions.
33. • An acid can be deprotonated by a base that has a conjugate
34
acid with a higher pKa.
• Because the pKa values of many carboxylic acids are ~5, bases
that have conjugate acids with pKa values higher than 5 are
strong enough to deprotonate them.
34.
35. • Carboxylic acids are relatively strong acids because
deprotonation forms a resonance-stabilized conjugate base—a
carboxylate anion.
• The acetate anion has two C—O bonds of equal length (1.27 Å)
and intermediate between the length of a C—O single bond
(1.36 Å) and C=O (1.21 Å).
36. • Ethoxide, the conjugate base of ethanol, bears a negative charge
on the O atom, but there are no additional factors to further
stabilize the anion. Because ethoxide is less stable than acetate,
ethanol is a weaker acid than acetic acid.
• Phenoxide, the conjugate base of phenol, is more stable than
ethoxide, but less stable than acetate because acetate has two
electronegative O atoms upon which to delocalize the negative
charge, whereas phenoxide has only one.
37. Figure 19.7
Summary: The relationship
between acidity and conjugate
base stability for acetic acid,
phenol, and ethanol
• Note that although resonance stabilization of the conjugate base is
important in determining acidity, the absolute number of resonance
structures alone is not what is important!
38. • Resonance stabilization accounts for why carboxylic
acids are more acidic than other compounds with O—H
bonds—namely alcohols and phenols.
• To understand the relative acidity of ethanol, phenol
and acetic acid, we must compare the stability of their
conjugate bases and use the following rule:
- Anything that stabilizes a conjugate base A:¯ makes the
39
starting acid H—A more acidic.