Alcohols and fermentation

Key idea: Alcohols contain a covalently bonded OH group. Yeast enzymes ferment glucose into ethanol and carbon dioxide in warm conditions with air excluded but gas able to escape.

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Alcohols are a homologous series of compounds containing the -OH group. Ethanol, the most familiar, is made by fermenting glucose with yeast. Carbon forms four bonds, hydrogen one and oxygen two, which is enough to draw any of the alcohols in this course.

Build and name alcohol structures

The simple alcohols studied here contain an -OH group bonded to a carbon that has only single bonds. The alcohols form a homologous series: they have the same -OH group, so they have similar chemical properties, and each member differs from the next by CH₂. Their names end in -ol.

To build an alcohol, take the alkane with the same number of carbons and replace one hydrogen with -O-H. The oxygen uses one bond to the carbon and one to its hydrogen.

Methanol, ethanol and propanol

Methanol is one carbon with three hydrogens and an O-H group. Ethanol is two carbons joined by a single bond; one carbon has three hydrogens and the other has two hydrogens and the O-H group. Propanol is a chain of three carbons joined by single bonds, with the O-H group on an end carbon.

Scroll across the figure to read all labels.

Displayed structures of methanol, ethanol and propanol, each with an O-H group on an end carbonDisplayed structures of methanol, ethanol and propanol, each with an O-H group on an end carbon
Each alcohol is an alkane with one hydrogen replaced by -O-H. In propanol the -O-H group is on an end carbon of the unbranched chain.
View figure data
Atoms in each displayed structure
AlcoholMolecular formulaCarbon atomsPosition of -OH
methanolCH₄O1on the carbon
ethanolC₂H₆O2on an end carbon
propanolC₃H₈O3on an end carbon
Carbon atomsNameMolecular formulaCondensed formula
1methanolCH₄OCH₃OH
2ethanolC₂H₆OCH₃CH₂OH or C₂H₅OH
3propanolC₃H₈OCH₃CH₂CH₂OH

Here, propanol means the end-group structure CH₃CH₂CH₂OH, more precisely named propan-1-ol.

The -OH group in an alcohol is covalently bonded to carbon. It is not a hydroxide ion, OH⁻; the presence of this group does not make a substance an alkali.

Check your understanding 1 Count the alcohol’s atoms and bonds

For ethanol, CH₃CH₂OH, count all carbon, hydrogen and oxygen atoms. Count the covalent bonds formed by its oxygen. Include the hydrogen in the alcohol group.

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Ethanol has molecular formula C₂H₆O. Its oxygen forms two covalent bonds, C–O and O–H. The bonded alcohol group is not a separate hydroxide ion. Now construct the complete structure and explain the bonding.

Check your understanding 2 Construct and explain ethanol’s bonding

Draw every atom and bond in ethanol on paper, describe the bonding and name its functional group. You need not transcribe the drawing.

Work on paper or in the optional notes. Compare a complete paper drawing with every C–H bond, the C–C bond, C–O–H and the covalent hydroxyl group.

Show answer

The two carbons share a single bond. One has three hydrogens; the other has two hydrogens and a bond to oxygen. Oxygen also bonds to one hydrogen. Each carbon has four bonds and oxygen has two. The functional group is -OH (hydroxyl).

Make ethanol by fermentation

Yeast converts glucose into ethanol and carbon dioxide. Enzymes in the yeast catalyse the reaction.

C₆H₁₂O₆ → (yeast) 2C₂H₅OH + 2CO₂
ConditionWhy it is needed
glucose dissolved in water, with yeastyeast enzymes act on dissolved glucose
warm, about 30–35 °Ccold slows the enzymes; too hot destroys (denatures) them and fermentation stops
no air (anaerobic)fermentation does not use oxygen; limiting air reduces competing aerobic respiration and helps protect the ethanol from oxidation

Keep air out while allowing carbon dioxide to escape, for example through a suitable fermentation airlock. Do not seal a gas-producing fermentation in a rigid, airtight bottle. Carbon dioxide would build up pressure. Excluding air helps produce and preserve ethanol; it does not mean yeast can never form any ethanol when oxygen is present.

Worked example 1

Read the fermentation equation

Problem

One mole of glucose ferments completely. Use the balanced equation to state the amounts of ethanol and carbon dioxide formed, and check that the equation balances.

Show solution step by step
  1. Read the coefficients

    Method

    Use the numbers in front of each formula.

    Reason

    The coefficients give the ratio of amounts in moles.

    Working

    Answer

    glucose : ethanol : carbon dioxide = 1 : 2 : 2

  2. Check the atoms balance

    Method

    Count each element on both sides.

    Reason

    A balanced equation conserves every atom.

    Working

    Answer

    Carbon: 6 = 2(2) + 2(1). Hydrogen: 12 = 2(6). Oxygen: 6 = 2(1) + 2(2).

  3. Answer

    Working

    Answer

    1 mol of glucose forms 2 mol of ethanol and 2 mol of carbon dioxide.

Guided practice 2

Set up a fermentation

About 4 min

Problem

A student wants to make ethanol from glucose solution and yeast. Choose the conditions, identify the gas and choose how it can escape safely.

Choose each condition

Temperature
Air
Gas given off
Keep air out while letting the gas escape

Hints

Hint 1

enzymes

Yeast contains enzymes.

Hint 2

equation

Look at the products in the fermentation equation.

Show full solution
  1. Conditions

    Working

    Answer

    Keep the mixture warm, at about 35 °C, and keep air out. Carbon dioxide bubbles off as the glucose ferments.

Check the structure before naming it

A learner calls ethanol an alkali because it contains -OH. The mistake is treating a covalently bonded group as a separate ion. The alcohol group is part of an uncharged molecule; an alkali produces OH⁻ ions in water.

Check your understanding 3 Explain the missing oxygen and the bonded group

What is wrong with giving ethanol the formula C₂H₆?

Work on paper or in the optional notes. Compare ethane with ethanol, total hydrogens and the oxygen introduced in C–O–H; compare a covalent group with a hydroxide ion.

Show answer

That is ethane’s formula. Replacing one C–H bond with C–O–H adds one oxygen while keeping the same total number of hydrogens. Ethanol has molecular formula C₂H₆O, often written C₂H₅OH to show the alcohol group.

Check your understanding 4 Name and count the complete propanol molecule

Name CH₃CH₂CH₂OH. How many covalent bonds does one molecule contain, and how many of them are C–H bonds?

Name

Show answer

It is propanol (propan-1-ol). There are 2 C–C bonds, 7 C–H bonds (3 + 2 + 2), 1 C–O bond and 1 O–H bond: 11 covalent bonds, 7 of them C–H. Check from the bonding rules: three carbons with four bonds, eight hydrogens with one and one oxygen with two give (12 + 8 + 2)/2 = 11 bonds, since each bond joins two atoms.

Worked example 3

Convert a mass through the fermentation ratio

Problem

Glucose of mass 18.0 g ferments completely. Find the ethanol mass using molar masses M(C₆H₁₂O₆) = 180 g mol⁻¹ and M(C₂H₅OH) = 46.0 g mol⁻¹.
Show solution step by step
  1. Convert glucose mass to amount

    Method

    Use n = m/M, where n is amount in moles, m mass and M molar mass.

    Reason

    The equation relates amounts in moles, not masses in grams.

    Working

    Answer

    n(C₆H₁₂O₆) = 18.0/180 = 0.100 mol.
  2. Apply the coefficient ratio

    Method

    Multiply by the ethanol-to-glucose ratio 2/1.

    Reason

    One mole of glucose forms two moles of ethanol.

    Working

    Answer

    n(C₂H₅OH) = 0.100(2) = 0.200 mol.
  3. Convert ethanol amount to mass

    Method

    Use m = nM with ethanol’s molar mass.

    Reason

    The target is a mass, not an amount.

    Working

    Answer

    m(C₂H₅OH) = 0.200(46.0) = 9.20 g.

Check your understanding 5 Convert, apply the ratio and convert back

Glucose of mass 90.0 g ferments completely. Use M(C₆H₁₂O₆) = 180 g mol⁻¹ and M(C₂H₅OH) = 46.0 g mol⁻¹. Find the glucose amount, apply the 1:2 glucose-to-ethanol mole ratio, then find the ethanol mass.

Unit: mol
Unit: mol
Show the steps Optional working
Unit: mol
Unit: mol
Unit: g

Show answer

The amounts are 0.500 mol glucose and 1.00 mol ethanol, giving 46.0 g ethanol. Now show the complete method and explain yeast’s role in the next activity.

Check your understanding 6 Explain the complete mass method and yeast’s role

90.0 g of glucose ferments completely. Calculate the mass of ethanol formed, and explain the role of yeast. Use M(C₆H₁₂O₆) = 180 g mol⁻¹ and M(C₂H₅OH) = 46.0 g mol⁻¹.

Work on paper or in the optional notes. Compare the mass–mole conversion, coefficient ratio, ethanol mass and yeast enzymes as catalysts.

Show answer

n(C₆H₁₂O₆) = 90.0/180 = 0.500 mol. The 1:2 glucose-to-ethanol ratio in C₆H₁₂O₆ → 2C₂H₅OH + 2CO₂ gives 1.00 mol ethanol, so the mass is 1.00(46.0) = 46.0 g. Enzymes in yeast catalyse the conversion of glucose to ethanol and carbon dioxide.

Check your understanding 7 Separate excluding air from trapping gas

A fermentation produces carbon dioxide. Choose what the setup should do with that gas and with incoming air.

Carbon dioxide produced
Incoming air

Show answer

A suitable airlock lets carbon dioxide out while keeping air out. Explain the problems with both the capped and open alternatives in the next activity.

Check your understanding 8 Explain both faulty fermentation setups

One student ferments glucose solution with yeast in a glass bottle with the cap screwed on tight. Another leaves the flask open to the air for a week. Predict a problem with each setup, and suggest a better one.

Work on paper or in the optional notes. Compare gas pressure in the tightly capped bottle, incoming oxygen in the open flask and the airlock’s two functions.

Show answer

In the capped bottle, carbon dioxide cannot escape, so pressure builds up and the bottle could burst. In the open flask, air gets in: aerobic respiration competes with fermentation, and the ethanol that forms can be oxidised. An airlock lets carbon dioxide out while keeping air out.

Common mistakes

  • Drawing the -OH group as a hydroxide ion, or as OH⁻.
  • Counting the carbons wrongly when naming, such as calling CH₃CH₂OH methanol.
  • Leaving out a fermentation condition: yeast, no oxygen and a warm temperature.
  • Writing the fermentation equation without carbon dioxide as a product.

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