Grade 12 ↓
Aldehydes, ketones and carboxylic acids
Aldehydes, ketones, and carboxylic acids are important classes of organic compounds that contain carbonyl groups. Understanding their structure, properties, and reactions is important for various applications in organic chemistry and industrial processes.
Aldehyde
Structure and nomenclature
Aldehydes are organic compounds containing a carbonyl group (C=O
) in which the carbon atom is bonded to at least one hydrogen atom. The general structure of an aldehyde is represented as R-CHO
, where R
is a hydrocarbon group or hydrogen.
Hey , H - C - R
In terms of nomenclature, aldehydes are named by identifying the longest carbon chain that contains the aldehyde group and replacing the terminal e
al
of the parent alkane with it. For example, the simplest aldehyde, methanal
, is commonly known as formaldehyde.
Example:
- HCHO: methanal (formaldehyde)
- CH3CHO: Ethanal (acetaldehyde)
- CH3CH2CHO: Propanal
Physical properties
- Due to the presence of the polar carbonyl group, the boiling point of aldehydes is generally higher than that of hydrocarbons of the same molecular weight.
- Low molecular weight aldehydes are soluble in water due to their ability to form hydrogen bonds.
- Aldehydes usually have a characteristic odor.
Chemical reactions
Aldehydes are very reactive compounds due to the presence of electron-deficient carbonyl carbon. Some common reactions are as follows:
1. Oxidation
Aldehydes can be easily oxidized to carboxylic acids. This reaction occurs easily in the presence of oxidizing agents like potassium dichromate (K2Cr2O7
), permanganate ion, etc.
R-CHO + [O] → R-COOH
2. Shortage
Aldehydes can be reduced to primary alcohols using reducing agents such as sodium borohydride (NaBH4
) or lithium aluminum hydride (LiAlH4
).
R-CHO + H2 → R-CH2OH
3. Condensation reactions
Aldehydes undergo condensation reactions with compounds containing active hydrogen atoms. An important reaction is the aldol condensation, where two aldehyde molecules combine to form β-hydroxy aldehyde.
2 R-CHO → [R-CH(OH)-CH2CHO]
Ketones
Structure and nomenclature
Ketones also contain a carbonyl group (C=O
) like aldehydes. However, the carbonyl carbon in ketones is bonded to two other carbon atoms. The general formula of ketones is R-CO-R'
, where R
and R'
are hydrocarbon groups.
Hey , R - C - R'
Ketones are named by replacing the terminal e
one
of the corresponding alkane. The simplest ketone, propanone
, is commonly known as acetone.
Example:
- CH3COCH3: Propanone (acetone)
- CH3COC2H5: Butanone
- C2H5COC2H5: Pentan-3-one
Physical properties
- Ketones have moderate boiling points, generally higher than similar hydrocarbons.
- Ketones with low molecular weight are soluble in water.
- Ketones have a variety of odors.
Chemical reactions
Ketones share some similarities with aldehydes in terms of reactivity, but are less reactive towards nucleophilic addition reactions.
1. Shortage
Ketones can be reduced to secondary alcohols using reducing agents such as sodium borohydride or lithium aluminium hydride.
R-CO-R' + H2 → R-CH(OH)-R'
2. Nucleophilic addition reactions
Ketones undergo nucleophilic addition reactions, where the nucleophile attacks the electrophilic carbon atom in the carbonyl group.
R-CO-R' + Neu → R-CHNeu-R'
3. Condensation reactions
Similar to aldehydes, ketones can also undergo aldol condensation reactions under appropriate conditions, forming β-hydroxy ketones.
2 R-CO-R' → [RC(OH)=R'-C-R']
Carboxylic acid
Structure and nomenclature
Carboxylic acids are organic compounds that contain a carboxyl group (-COOH
) as the functional group. The general formula is R-COOH
, where R
can be a hydrogen atom, an alkyl group, or another arene group.
Hey , R – C , Oh
Carboxylic acids are named by replacing the terminal e
oic acid
of the parent alkane. The simplest carboxylic acid is methanoic acid, also known as formic acid.
Example:
- HCOOH: Methanoic acid (formic acid)
- CH3COOH: Ethanoic acid (acetic acid)
- CH3CH2COOH: Propanoic acid
Physical properties
- Carboxylic acids have high boiling point due to hydrogen bonding between the molecules.
- Lower carboxylic acids are highly soluble in water.
- They generally have acidic properties and a characteristic pungent or sour odor.
Chemical reactions
Carboxylic acids are known for their reactivity and ability to undergo a wide range of chemical transformations:
1. Acid-base reactions
Carboxylic acids can deprotonate to form carboxylate ions, which shows their weak acidic nature.
R-COOH ⇌ R- COO- + H +
2. Esterification
In the presence of alcohol and acid catalysts, carboxylic acids react to form esters.
R-COOH + R'OH ⇌ R-COOR' + H2O
3. Shortage
Carboxylic acids can be reduced to primary alcohols using strong reducing agents such as LiAlH4
.
R-COOH + H2 → R-CH2OH
4. Formation of anhydride
A carboxylic acid can condense with another carboxylic acid molecule to form an anhydride.
2 R-COOH → R-COO-COR + H2O
Conclusion
Aldehydes, ketones, and carboxylic acids are fundamental building blocks in organic chemistry. Aldehydes are generally more reactive than ketones because of the hydrogen atom attached to the carbonyl group, which allows them to engage in further reactions such as oxidation. Ketones are generally less reactive due to the two carbon groups attached. Carboxylic acids containing acidic hydroxyl groups can give rise to a variety of reactions, including esterification and reduction.
Understanding these compounds plays a vital role in various chemical industries, including the production of flavors, fragrances, polymers, pharmaceuticals, and many other applications. Therefore, it is important for any aspiring chemist to master their structure, nomenclature, properties, and reactions.