Exam Practice

Topic 3.3.5: Alcohols Exam Practice

Test your understanding of ethanol production, oxidation pathways, Fehling/Tollens tests, and alcohol dehydration mechanisms with exam-style questions.

Alcohols Exam Practice

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📋 Structured Questions

Complete each question on paper, then check your answers against the mark scheme.

Question 1: Production of Ethanol

5 marks

(a) Write equations for the fermentation of glucose, and the subsequent complete combustion of the ethanol produced. [2]

(b) Fermentation of glucose is often described as producing a "carbon-neutral" biofuel. Support this statement by writing an overall equation showing the balance of carbon dioxide taken in and released, assuming photosynthesis forms the glucose. [2]

(c) Give one reason why this process is not strictly carbon-neutral in practice. [1]

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(a)

  • Fermentation: C6H12O6 -> 2C2H5OH + 2CO2 [1]
  • Combustion: C2H5OH + 3O2 -> 2CO2 + 3H2O [1]

(b)

  • Photosynthesis: 6CO2 + 6H2O -> C6H12O6 + 6O2 (takes in 6 CO2) [1]
  • Fermentation + Combustion: (2 CO2 from fermentation) + (2 x 2 CO2 from burning 2 molecules of ethanol) = 6 CO2 released. Net balance is zero. [1]

(c)

  • Carbon dioxide is released by burning fossil fuels to power machinery for farming, transporting crops/fuel, and heating the fractional distillation column to purify the ethanol. [1]
Examiner tip: To get full marks for the carbon-neutral argument, show the maths: 6 CO2 absorbed in photosynthesis equals 2 CO2 (fermentation) + 4 CO2 (combustion) released.

Question 2: Oxidation and Chemical Tests

5 marks

A student has three unlabelled bottles containing propan-1-ol, propan-2-ol, and 2-methylpropan-2-ol.

(a) Describe a chemical test (including reagents and observations) that could identify which bottle contains 2-methylpropan-2-ol. [2]

(b) The student oxidizes the other two alcohols. Describe how the student could use Tollens' reagent or Fehling's solution to distinguish between the oxidation products of propan-1-ol and propan-2-ol. Include expected observations. [3]

Show Mark Scheme

(a)

  • Add acidified potassium dichromate(VI) (K2Cr2O7/H2SO4) and warm. [1]
  • The bottle containing 2-methylpropan-2-ol (a tertiary alcohol) will show no reaction and remain orange. The other two bottles (containing primary/secondary alcohols) will turn from orange to green. [1]

(b)

  • Oxidation of propan-1-ol yields propanal (an aldehyde). Oxidation of propan-2-ol yields propanone (a ketone). [1]
  • Add Tollens' reagent (or Fehling's solution) and warm. [1]
  • Observations: The oxidation product of propan-1-ol (propanal) forms a silver mirror (or red precipitate with Fehling's). The oxidation product of propan-2-ol (propanone) shows no reaction. [1]
Examiner tip: Ensure you state that the products of oxidation are tested, not the alcohols themselves. Tollens' and Fehling's reagents do not react with alcohols.

Question 3: Dehydration Mechanism

4 marks

Write the mechanism for the dehydration of cyclohexanol to form cyclohexene in the presence of a concentrated phosphoric acid catalyst (H3PO4, acting as a source of H+ ions). Include all curly arrows, lone pairs, and formal charges. [4]

Show Mark Scheme
  • Step 1: Curly arrow from the lone pair on the oxygen atom of the cyclohexanol -OH group to the catalyst H+ proton. [1]
  • Intermediate 1: Correct structure of protonated cyclohexanol (with -OH2+ group, positive charge on oxygen). [1]
  • Step 2: Curly arrow from the C-O bond to the positive oxygen atom, representing loss of a water molecule. [1]
  • Step 3: Correct carbocation intermediate (cyclohexyl ring with C+). Curly arrow from a C-H bond on an adjacent carbon atom into the adjacent C-C bond to form the C=C double bond (cyclohexene) and release H+. [1]
Examiner tip: For elimination mechanisms of alcohols, make sure the protonated intermediate has the positive charge on the oxygen, and the subsequent carbocation has the positive charge on the carbon. Always show the H+ regenerated at the end.

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