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ESO Y4A · Physics and Chemistry
Matter · Chemical nomenclature

"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.

Before you start, make sure you know: The atomic-molecular model (3rd ESO)
Before you start, make sure you know: Algebraic expressions (2nd ESO)

What an organic compound is

Diagram of an open chain of four carbon atoms bonded in a zigzag, with hydrogens attached to each carbon C C C C carbon (C) hydrogen (H) carbon chain: the basis of organic chemistry
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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, $\text{C}_2\text{H}_6\text{O}$.

  1. a) State which of these substances are organic compounds and which are not.
  2. b) Explain in your own words which element is the "backbone" of organic chemistry.
Solve

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?

Ethane molecule, C₂H₆: two carbon atoms joined by a single bond and each carbon also bonded to three hydrogens, so that each carbon forms four bonds C C H H H H H H single bond C–H bond ethane, C₂H₆ each C forms 4 bonds: 1 with C and 3 with H
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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.

C H H H H CH₄ C C H H H H H H C₂H₆ C C C H H H H H H H H C₃H₈ C C C C H H H H H H H H H H C₄H₁₀
  1. a) $\text{CH}_4$
  2. b) $\text{C}_2\text{H}_6$
  3. c) $\text{C}_3\text{H}_8$
  4. d) $\text{C}_4\text{H}_{10}$
  1. e) Explain what the prefix (meth-, eth-, prop-, but-) indicates and what the suffix -ane indicates.
Solve
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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.

  1. a) Check that this holds true for methane ($n = 1$) and for butane ($n = 4$).
  2. b) Work out the molecular formula of the alkane with $5$ carbon atoms, called pentane.
Solve

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?

Comparison of the ethane, ethene and ethyne molecules: two carbon atoms joined by a single, double or triple bond, with six, four and two hydrogen atoms respectively H H H H H H C C ethane, C₂H₆ alkane: single C–C bond 6 H atoms H H H H C C ethene (ethylene), C₂H₄ alkene: double C=C bond 4 H atoms H H C C ethyne (acetylene), C₂H₂ alkyne: triple C≡C bond 2 H atoms
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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, $\text{C}_2\text{H}_4$.

  1. a) What type of bond joins its two carbon atoms: single, double or triple?
  2. b) Which family does it belong to?
Solve
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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, $\text{C}_n\text{H}_{2n-2}$.

  1. a) Work out the molecular formula of propene (an alkene with $3$ carbon atoms).
  2. b) Work out that of propyne (an alkyne with $3$ carbon atoms).
  3. c) Explain why ethene cannot have the formula $\text{C}_2\text{H}_6$.
Solve
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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 $\text{C}_4\text{H}_8$.

  1. a) Using the general formulas, state which is an alkane and which is an alkene.
  2. b) Name the alkane.
  3. c) Could either of the two be an alkyne? Justify your answer using the general formula $\text{C}_n\text{H}_{2n-2}$.
Solve

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?

Structural formulae of methane and methanol: replacing one hydrogen atom of methane with the functional group –OH (hydroxyl) gives methanol, an alcohol C H H H H H being replaced substitution H by –OH C H H H O H functional group –OH (hydroxyl) methane: CH₄ hydrocarbon methanol: CH₃OH alcohol
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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.

  1. a) What group of atoms do both formulas share?
  2. b) What is this functional group called and which family do both compounds belong to?
Solve
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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, $\text{C}_2\text{H}_6$.

  1. a) Explain why ethanol is not considered a hydrocarbon, even though it is so similar to ethane.
  2. b) Which family does ethanol belong to and what is its functional group?
Solve
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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.

  1. a) Apply this idea to methane and write the condensed structural formula of methanol.
  2. b) Do the same with ethane and write that of ethanol.
  3. c) Also write the molecular formulas of both alcohols.
Solve

Another functional group: carboxylic acids

Ethanoic acid molecule, CH₃COOH, in a ball-and-stick model: on the left the methyl group and on the right the carboxyl group −COOH, with two carbon atoms in total ethanoic acid (acetic acid) C C O O H H H H methyl group carboxyl group CH₃ – COOH 2 carbons in total (the one in −COOH counts too): C₂H₄O₂
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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, $\text{CH}_3\text{COOH}$.

  1. a) Count how many carbon, hydrogen and oxygen atoms its molecule has and write its molecular formula (all atoms together, without separating by groups).
  2. b) Indicate in the formula the $-\text{COOH}$ functional group characteristic of carboxylic acids.
Solve
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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:

  1. a) $\text{CH}_3\text{OH}$
  2. b) $\text{CH}_3\text{CH}_2\text{OH}$
  3. c) $\text{CH}_3\text{COOH}$
Solve
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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.

  1. a) Write the condensed structural formula of each and name them according to IUPAC.
  2. b) Circle the functional group in each formula and state its name.
  3. c) State an everyday substance in which each one is found.
Solve

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:

Structural formulae of four simple molecules with the functional group highlighted: ethanol (alcohol), methoxymethane (ether), propanal (aldehyde, carbonyl at the end) and propanone (ketone, inner carbonyl) Alcohol Ether Aldehyde Ketone C C O H C O C C C C O H C C C O C–O–H · ethanol C–O–C · methoxymethane C–CHO · propanal C–CO–C · propanone H atoms bonded to carbon are not drawn.

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.

Summary

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