Hydrocarbon Derivatives

(Aldehydes, Ketones, Carboxylic Acids, Esters, Amines, and Amides)

1. Aldehydes (RCHO)
- a hydrocarbon derivative that contains a formyl group.
- Figure A shows a carbonyl group where a carbon atom is double bonded to an oxygen
atom.
- Figure B shows a formyl, contains a carbonyl group and a hydrogen atom.
- this group is always found at the end of a hydrocarbon chain.
- most basic aldehyde is formaldehyde or methanal.

Physical Properties:
- cannot hydrogen bond with one another but they can hydrogen bond with water.
- boiling points are lower than those of alcohols.
- water solubility depends on carbon length, short chains are more soluble.
- Short chain smells pungent while longer chains have a more pleasant odor.

Naming Aldehydes:



2. Ketones (RCR)
- a hydrocarbon derivative that contains a carbonyl group that is bonded to two carbon
atoms or carbon chains.
- Acetone is the common name for the ketone, propanone, it is used to remove nail
polish from fingernails, ink stains from fingers, as well as pricetag stickers from glass, metal, or
porcelain objects.
- Because the carbonyl carbon in ketones must be bonded to two other carbon atoms,
the smallest ketone must have at least three carbon atoms.






Physical Properties
Can hydrogen bond with water
Similar boiling point and solubilitiy with aldehydes
Smaller ketones are liquid at room temperature, 15 carbon chains or higher are waxy.
Naming Ketones



3. Carboxylic Acids ( RCOOH )
- A carboxylic acid is an organic compound that contains a carboxyl group.
- are acidic because of the hydrogen in the COOH group
- examples: ethanoic acid / acetic acid in vinegar, citric acid, tartaric acid




Physical Properties:
Very polar, can hydrogen bond with one another.
Weak acids
Short chains are liquids at room temperature and are soluble in water; longer chains are
waxy, less soluble in water

Naming Carboxylic Acids


4. Esters ( RCOOR )
- A hydrocarbon derivative that contains a functional group with a carbon atom
double bonded to one oxygen atom and single bonded to one another.
- The general formula for an ester is RCOOR'. The symbol R represents any
hydrocarbon or just a hydrogen atom. The symbol R' represents a hydrocarbon and,
therefore, it must contain at least one carbon atom.
- Esters can be thought of as the product of a reaction between a carboxylic acid
and an alcohol.

Physical Properties:
- Esters are more polar than ethers but less polar than alcohols.
- lower boiling point than alcohols and carboxylic acids.
- short chains are liquids; longer chains are waxy at room temperature
- are more volatile than carboxylic acids of similar molecular weight.
- responsible for the aroma of many fruits, including apples, durians, pears,
bananas, pineapples, and strawberries.
- extensive use in the fragrance and flavor industry

Naming Esters




5. Amines (RNRR)
- are organic compounds and functional groups that contain a basic nitrogen
atom with a lone pair.
- Amines are derivatives of ammonia, wherein one or more hydrogen atoms have
been replaced by a substituent such as an alkyl or aryl group.
- Important amines include amino acids, biogenic amines, trimethylamine, and
aniline
- Primary amines have one carbon atom bonded to the nitrogen, secondary
amines have two, and tertiary amines have three.


Physical Properties:

- The N-H bonds of primary and secondary amines are very polar; tertiary have
none.
- Primary and secondary amines have higher boiling points compared to ethers,
alkanes and tertiary amines.
- All amines can hydrogen bond with water, therefore soluble in water especially
smaller amines.
- Gaseous amines possess a characteristic ammonia smell, liquid amines have a
distinctive "fishy" smell
Naming Amines
























6. Amides (RCONRR)
- also known as an acid amide, is a compound with the functional group RCONRR.
- Amides are commonly formed via reactions of a carboxylic acid with an amine.








- Most common commercial uses of amides, are in polymers such as nylon and
polyacrylamide.
- In the general formula, R, R, and R can represent the same or different alkyl groups,
but they can also represent hydrogen atoms.
- A primary amide has two hydrogen atoms bonded to the nitrogen atom. A secondary
amide has one hydrogen and one alkyl group bonded to the nitrogen atom. A tertiary amide has
two alkyl groups bonded to the nitrogen atom.





Physical Properties:
- Amides have a polar carbonyl group and primary and secondary amides have
at least one NH group. Therefore, they can form strong hydrogen bonds among
themselves.









Naming Amides




























Hydrocarbon Derivatives with Multiple Functional Groups
Priority List










Here are some examples of applying the order of functional group priorities
to solve nomenclature problems. The highest ranked functional group
becomes the suffix its highlighted in red.





Polarity among hydrocarbon derivatives

amide > acid > alcohol > ketone aldehyde > amine > ester > ether >
alkane