Aldehydes, Ketones, Carboxylic Acids: R-COH Aldehyde R-CO-R Ketone R-Cooh

R-COH aldehyde
R-CO-R ketone
R-COOH
Aldehydes, ketones, carboxylic
acids
Aldehydes and ketones are classes of organic compounds that contain
a carbonyl (C=O) group.
Nomenclature:
Aldehydes: functional group suffix = -al
Ketones: functional group suffix = -one
(Note that an aldehyde is higher priority than a ketone)
Physical Properties:
The polar nature of the C=O (due to the electronegativity difference of the atoms)
means dipole-dipole interactions will occur.
Though C=O can not hydrogen-bond to each other, the C=O can accept hydrogen
bonds from hydrogen bond donors (e.g. water, alcohols).
Structure:The carbonyl group consists of an O atom bonded to a C atom via a double

bond, C=O, via an sp2 hybridisation model similar to that of ethene, H2C=CH2 with
bond angles close to 120o.
O is connected to the carbonyl C via a σ and a π bond.
The C=O and the two other atoms attached to the C are co-planar.
This implies that the two lone pairs on O are in sp2 hybrid orbitals.
The image shows the electrostatic potential for methanal (formaldehyde)
The more red an area is, the higher the electron density and the more blue an
area is, the lower the electron density. The O atom in the C=O is a region of high
electron density (red) due to the lone pairs.
•The carbonyl oxygen atoms are Lewis bases (site of protonation)
•There is low electron density (blue) on the C atom of the C=O group.
The image shows the electrostatic potential for

propanone (acetone).
The more red an area is, the higher the electron density
and the more blue an area is, the lower the electron
density. The O atom in the C=O is a region of high
electron density (red) due to the lone pairs.
•The carbonyl oxygen atoms are Lewis bases (site of
protonation)
•There is low electron density (blue) on the C atom of
the C=O group
Methanoic acid
methanal
ethanal
Ethanoic acid
Oxidation-addition of oxygen or removal of hydrogen
Reduction-removal of oxygen or addition of hydrogen
Hydration
R-COH + HOH ↔ R-CH (OH)2 unstable diols
Hydrogenation
R-COH + H2 → R-CH2OH-primary alcohol
RR’CO (ketone) +H2 → RR’CHOH (secondary alcohol)
CH3-CO-CH3 + H2 =CH3-CHOH-CH3 =propanol-2
CH3-CH2-CH2CO-CH2-CH2-CH3+H2 =CH3-CH2-CH2OH-CH2-CH2-CH3
acetone
Oxidation
R-COH + Ag2O =R-COOH + 2Ag
HCOH +2Ag2O =CO2 + 2Ag + H2O
Polymerization
CH3-CO-CH3 acetone
CH4 +O2 (500oC, cat)=HCOH + H2O
Preparation 2CH3OH +O2 (Cu or Ag)=2HCOH + 2H2O
1. By oxidation of alcohols (300oC, Cu): HC≡CH + H2O (Hg2+) = CH3COH

O 2CH2=CH2 +O2 (Cu, Fe, Pd salts) 2CH3COH
R-CH2OH +[O] R-C
-H2O H
R-CHOH-R’ +[O] R-CO-R’ + H2O
R-CH2OH R-COH +H2

R-CHOH-R’ R-CO-R’ + H2 aldehyde - “alcoholdehydrogenatum”
2. Alkenes oxidation (PdCl2, CuCl2, 100oC, 0.3 Mpa):

CH2=CH2 +[O] CH3COH
Naming Aldehydes
The IUPAC system of nomenclature assigns a characteristic suffix -al to
aldehydes. For example, H2C=O is methanal, more commonly called
formaldehyde. Since an aldehyde carbonyl group must always lie at the
end of a carbon chain, it is always is given the #1 location position in
numbering and it is not necessary to include it in the name. There are
several simple carbonyl containing compounds which have common
names which are retained by IUPAC.
Aldehydes take their name from their parent alkane chains. The -e is
removed from the end and is replaced with -al.
The aldehyde funtional group is given the #1 numbering location and
this number is not included in the name.
For the common name of aldehydes start with the common parent
chain name and add the suffix -aldehyde. Substituent positions are
shown with Greek letters.
Naming Ketones
The IUPAC system of nomenclature assigns a characteristic suffix of -
one to ketones. A ketone carbonyl function may be located anywhere
within a chain or ring, and its position is usually given by a location
number. Chain numbering normally starts from the end nearest the
carbonyl group. Very simple ketones, such as propanone and
phenylethanone do not require a locator number, since there is only
one possible site for a ketone carbonyl function
The common names for ketones are formed by naming both alkyl
groups attached to the carbonyl then adding the suffix -ketone. The
attached alkyl groups are arranged in the name alphabetically.
Summary of Ketone Nomenclature rules
Ketones take their name from their parent alkane chains. The ending -
e is removed and replaced with -one.
The common name for ketones are simply the substituent groups
listed alphabetically + ketone.
Some common ketones are known by their generic names. Such as
the fact that propanone is commonly referred to as acetone.
CH3-CH2-CO-CH2-CH2-CH3
Hexanone-3
CH3-CH2-CH2-CO-CH2-CH3
Dimethyl ketone
CH3-CH2-CH2-CO-CHCl-CHCH3-CH3
5-chloro-6-methyl-heptanone-4 mistake
3-chloro-2-methyl-heptanone-4
CH3-CH2-COH +H2= CH3-CH2-CH2OH prop
R-COH +H2= R-CH2OH primary alcohol
R-CO-R +H2 =R-CHOH-R secondary alcohol

CH3-CH2-CHOH-CH2-CH3 pentanol-3
R-C(R)OH-R.
CH3-CH2-CH(CH3)(OH)-CH2-CH2-CH3-tertiary alcohol
3-methyl-hexanol-3
The ease of oxidation helps chemists identify aldehydes. A sufficiently mild
oxidizing agent can distinguish aldehydes not only from ketones but also
from alcohols. Tollens’ reagent, for example, is an alkaline solution of silver
(Ag+) ion complexed with ammonia (NH3), which keeps the Ag+ ion in
solution.
H3N—Ag+—NH3
When Tollens’ reagent oxidizes an aldehyde, the Ag+ ion is reduced to free
silver (Ag). Silver mirror reaction
R-COH + 2[Ag(NH3)2]OH = R-COOH + 2Ag + 4NH3 +H2O

silverdiammine hydroxide
Ag2O, AgOH. AgNO3 +NaOH=AgOH +NaNaO3

AgOH +2NH3 (NH4OH)= [Ag(NH3)2]OH
R-COH + 2Cu(OH)2 = R-COOH + 2CuOH↓+ H2O

2CuOH = Cu2O + H2O
F,O, N
Carboxylic acids Octet rule-each atom has affinity to has complete shell (8-electron
Containing carboxyl functional group –COOH

R-COOH or CnH2n+1COOH 11Na 1s22s22p63s1
9F 1s22s22p5
HCOH-formaldehyde -methanal
HCOOH –formic acid-metanoic acid
CH3COOH acetic acid- ethanoic acid
CH3CH2COOH propanoic acid
CH3(CH2)2COOH
CH3(CH2)3COOH
CH3(CH2)4COOH
CH3(CH2)5COOH
CH3(CH2)6COOH
CH3(CH2)14COOH Palmitic acid
CH3(CH2)14COONa soaps goat fat + KOH (ash)
CH3(CH2)16COOH Stearic acid
Obtaining
Oxidation of alcohols or aldehydes
O
R-CH2OH +[O] = R-COH RCOOH
2. Nitriles hydrolisis
R-C≡N + 2H2O R-COOH + NH3
3. Trihalogenalkanes hydrolysis
R-CCl3 +3NaOH R-COOH +3NaCl
CH3COONa
4. Interaction of corresponding salts with sulphuric acid
2R-COONa + H2SO4 2R-COOH + Na2SO4
CH3COONa H2SO4 =Na2SO4 + CH3COOH
Pherment oxidation of wine alcohol to aldehyde
CH3-CH2OH +O2 [aldehyde, acetaldehyde] → CH3COOH + H2
Chemical properties
Formation of salts
2R-COOH + Mg → (R-COO)2Mg + H2
Na=R-COONa, (CH3COO)2Mg
2R-COOH + ZnO → (R-COO)2Zn + H2O

R-COOH + NaOH → R-COONa + H2O
R-COOH + Mg → (R-COO)2Mg + H2
With alcohols form esters

R-COOH + HO-R’=R-COO-R’ +H2O
R-OH + HO-R’=R-O-R’ +H2O ethers –intermolecular dehydration
R-CH2-CH2-OH=R-CH=CH2 + H2O intramolecular dehydration
CH3-O-CH3 dimethyl ether
CH3-O-CH2-CH3 ethylmethyl ether
CH3COO-CH2CH3 ethylethanoate CH3CH2COO-CH3 methylpropanoate
CH2OH-CHOH-CH2OH glycerin
+ 3 palmitic acid (C-16)
CH2OOC(CH2)14CH3 tryglycerides (fats)

Aldehydes, Ketones, Carboxylic Acids: R-COH Aldehyde R-CO-R Ketone R-Cooh

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Aldehydes, Ketones, Carboxylic Acids: R-COH Aldehyde R-CO-R Ketone R-Cooh

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R-COH aldehyde

(Note that an aldehyde is higher priority than a ketone)

Structure:The carbonyl group consists of an O atom bonded to a C atom via a double

The image shows the electrostatic potential for

1. By oxidation of alcohols (300oC, Cu): HC≡CH + H2O (Hg2+) = CH3COH

R-CHOH-R’ +[O] R-CO-R’ + H2O

R-CH2OH R-COH +H2

2. Alkenes oxidation (PdCl2, CuCl2, 100oC, 0.3 Mpa):

R-COH +H2= R-CH2OH primary alcohol

R-CO-R +H2 =R-CHOH-R secondary alcohol

R-COH + 2[Ag(NH3)2]OH = R-COOH + 2Ag + 4NH3 +H2O

Ag2O, AgOH. AgNO3 +NaOH=AgOH +NaNaO3

R-COH + 2Cu(OH)2 = R-COOH + 2CuOH↓+ H2O

Containing carboxyl functional group –COOH

2R-COOH + ZnO → (R-COO)2Zn + H2O

With alcohols form esters

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