"Introduction to organic nomenclature: monofunctional compounds"
The gas in a kitchen hob, the alcohol used on cuts and the vinegar on a salad have something in common that table salt does not: they are all built from a chain of carbon atoms. That chain is the backbone of organic chemistry.
What an organic compound is
Natural gas for cooking is methane, $\text{CH}4$; tap water is $\text{H}2\text{O}$; a lighter contains butane, $\text{C}4\text{H}{10}$; salt is $\text{NaCl}$ and rubbing…
Natural gas for cooking is methane, $\text{CH}_4$; tap water is $\text{H}_2\text{O}$; a lighter contains butane, $\text{C}_4\text{H}_{10}$; salt is $\text{NaCl}$ and rubbing alcohol is ethanol, $\text{C}_2\text{H}_6\text{O}$.
- a) State which of these substances are organic compounds and which are not.
- b) Explain in your own words which element is the "backbone" of organic chemistry.
Saturated hydrocarbons: the alkanes
When we measure the composition of natural gas (methane, $\text{CH}_4$), lighter gas (butane, $\text{C}_4\text{H}_{10}$) and candle wax (paraffin, $\text{C}_{20}\text{H}_{42}$), we find that the number of hydrogens always keeps a fixed proportion to the number of carbons: what geometric rule determines how many hydrogens fit on a chain with no double bonds?
Name these four hydrocarbons: The figure shows the molecular models of all four. a) $\text{CH}4$ b) $\text{C}2\text{H}6$ c) $\text{C}3\text{H}8$ d)…
Name these four hydrocarbons:
The figure shows the molecular models of all four.
- a) $\text{CH}_4$
- b) $\text{C}_2\text{H}_6$
- c) $\text{C}_3\text{H}_8$
- d) $\text{C}_4\text{H}_{10}$
- e) Explain what the prefix (meth-, eth-, prop-, but-) indicates and what the suffix -ane indicates.
All alkanes follow the general formula $\text{C}n\text{H}{2n+2}$, where $n$ is the number of carbon atoms. a) Check that this holds true for methane ($n = 1$) and for…
All alkanes follow the general formula $\text{C}_n\text{H}_{2n+2}$, where $n$ is the number of carbon atoms.
- a) Check that this holds true for methane ($n = 1$) and for butane ($n = 4$).
- b) Work out the molecular formula of the alkane with $5$ carbon atoms, called pentane.
Alkenes and alkynes: double and triple bonds
Ethene ($\text{C}_2\text{H}_4$), which ripe fruit gives off, and ethyne ($\text{C}_2\text{H}_2$), used in welding torches, have two carbons just like ethane ($\text{C}_2\text{H}_6$), but fewer hydrogens: how do they manage to bond stably if there are not enough hydrogen atoms to bond to?
Fruit naturally releases a gas that accelerates its ripening: ethene, $\text{C}2\text{H}4$. a) What type of bond joins its two carbon atoms: single, double or triple? b)…
Fruit naturally releases a gas that accelerates its ripening: ethene, $\text{C}_2\text{H}_4$.
- a) What type of bond joins its two carbon atoms: single, double or triple?
- b) Which family does it belong to?
Alkenes follow the general formula $\text{C}n\text{H}{2n}$ and alkynes, $\text{C}n\text{H}{2n-2}$. a) Work out the molecular formula of propene (an alkene with $3$…
Alkenes follow the general formula $\text{C}_n\text{H}_{2n}$ and alkynes, $\text{C}_n\text{H}_{2n-2}$.
- a) Work out the molecular formula of propene (an alkene with $3$ carbon atoms).
- b) Work out that of propyne (an alkyne with $3$ carbon atoms).
- c) Explain why ethene cannot have the formula $\text{C}_2\text{H}_6$.
Two compounds with $4$ carbon atoms have formulas $\text{C}4\text{H}{10}$ and $\text{C}4\text{H}8$. a) Using the general formulas, state which is an alkane and which is…
Two compounds with $4$ carbon atoms have formulas $\text{C}_4\text{H}_{10}$ and $\text{C}_4\text{H}_8$.
- a) Using the general formulas, state which is an alkane and which is an alkene.
- b) Name the alkane.
- c) Could either of the two be an alkyne? Justify your answer using the general formula $\text{C}_n\text{H}_{2n-2}$.
The functional group: alcohols
Ethane ($\text{C}_2\text{H}_6$) is a non-polar gas that does not mix with water, but if we replace a single hydrogen atom with an oxygen and a hydrogen we get ethanol ($\text{C}_2\text{H}_5\text{OH}$), a liquid that dissolves in water in any proportion: how can a single group of atoms completely change the behaviour of a molecule?
Methanol, $\text{CH}3\text{OH}$, is used as fuel in some model engines and ethanol, $\text{CH}3\text{CH}2\text{OH}$, is the alcohol in disinfectants. a) What group of…
Methanol, $\text{CH}_3\text{OH}$, is used as fuel in some model engines and ethanol, $\text{CH}_3\text{CH}_2\text{OH}$, is the alcohol in disinfectants.
- a) What group of atoms do both formulas share?
- b) What is this functional group called and which family do both compounds belong to?
Ethanol has the molecular formula $\text{C}2\text{H}6\text{O}$ and ethane, $\text{C}2\text{H}6$. a) Explain why ethanol is not considered a hydrocarbon, even though it…
Ethanol has the molecular formula $\text{C}_2\text{H}_6\text{O}$ and ethane, $\text{C}_2\text{H}_6$.
- a) Explain why ethanol is not considered a hydrocarbon, even though it is so similar to ethane.
- b) Which family does ethanol belong to and what is its functional group?
An alcohol can be imagined as an alkane in which a hydrogen atom has been replaced by an $-\text{OH}$ group. a) Apply this idea to methane and write the condensed…
An alcohol can be imagined as an alkane in which a hydrogen atom has been replaced by an $-\text{OH}$ group.
- a) Apply this idea to methane and write the condensed structural formula of methanol.
- b) Do the same with ethane and write that of ethanol.
- c) Also write the molecular formulas of both alcohols.
Another functional group: carboxylic acids
The sour taste of vinegar is due to acetic acid, whose IUPAC name is ethanoic acid, $\text{CH}3\text{COOH}$. a) Count how many carbon, hydrogen and oxygen atoms its…
The sour taste of vinegar is due to acetic acid, whose IUPAC name is ethanoic acid, $\text{CH}_3\text{COOH}$.
- a) Count how many carbon, hydrogen and oxygen atoms its molecule has and write its molecular formula (all atoms together, without separating by groups).
- b) Indicate in the formula the $-\text{COOH}$ functional group characteristic of carboxylic acids.
Indicate the functional group of each compound and state which family it belongs to: a) $\text{CH}3\text{OH}$ b) $\text{CH}3\text{CH}2\text{OH}$ c)…
Indicate the functional group of each compound and state which family it belongs to:
- a) $\text{CH}_3\text{OH}$
- b) $\text{CH}_3\text{CH}_2\text{OH}$
- c) $\text{CH}_3\text{COOH}$
In the laboratory there are two bottles: one contains the alcohol with $2$ carbon atoms and the other contains the carboxylic acid with $2$ carbon atoms. a) Write the…
In the laboratory there are two bottles: one contains the alcohol with $2$ carbon atoms and the other contains the carboxylic acid with $2$ carbon atoms.
- a) Write the condensed structural formula of each and name them according to IUPAC.
- b) Circle the functional group in each formula and state its name.
- c) State an everyday substance in which each one is found.
Recognising other functional groups
The molecular formula alone does not determine the functional group. In these simple molecules we choose a chain that includes the group and number it so as to place the group correctly.
| Family | Characteristic group | Example and name |
|---|---|---|
| Aldehyde | $-\text{CHO}$ | $\text{CH}_3\text{CHO}$, ethanal |
| Ketone | $-\text{CO}-$ inside the chain | $\text{CH}_3\text{COCH}_3$, propanone |
| Ether | $-\text{O}-$ between carbons | $\text{CH}_3\text{OCH}_3$, methoxymethane |
| Ester | $-\text{COO}-$ | $\text{CH}_3\text{COOCH}_3$, methyl ethanoate |
| Amine | $-\text{NH}_2$ in primary cases | $\text{CH}_3\text{NH}_2$, methanamine |
Propanone is used as a solvent and some esters give off pleasant aromas. An everyday use does not mean that a substance can be tasted or smelled directly: follow its safety instructions.
The diagram sums up the main ideas:
Back to the start: Cooking gas (butane, $\text{C}_4\text{H}_{10}$, an alkane), pharmacy alcohol (ethanol, $\text{C}_2\text{H}_5\text{OH}$) and vinegar (ethanoic acid, $\text{CH}_3\text{COOH}$) share carbon skeletons, but the presence of different functional groups transforms a fuel into an antiseptic or into an edible condiment.