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Cumin is a spice used to flavour food - CIE - A-Level Chemistry - Question 8 - 2018 - Paper 1

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Cumin is a spice used to flavour food. Two compounds responsible for its flavour are cuminaldehyde and cumyl alcohol. (i) Deduce the number of peaks that would be p... show full transcript

Worked Solution & Example Answer:Cumin is a spice used to flavour food - CIE - A-Level Chemistry - Question 8 - 2018 - Paper 1

Step 1

i) Deduce the number of peaks that would be present in the 13C NMR spectrum of cumyl alcohol.

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Answer

The 13C NMR spectrum of cumyl alcohol would display a total of 7 peaks. This is due to the distinct carbon environments within the molecule.

Step 2

ii) Identify two bonds that are responsible for the differences in the infra-red spectra of cuminaldehyde and cumyl alcohol, and state their absorption ranges.

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Bond ResponsibleAbsorption Range (cm⁻¹)
C=O (in cuminaldehyde)1670-1740
O-H (in cumyl alcohol)3200-3600
C-O (in cumyl alcohol)1000-1260

Step 3

i) Suggest reagents and conditions for steps 1–4.

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Step 1: Heat with AlCl₃; (CH₃)₂CHCl or CH₃CH₂Cl Step 2: Heat with AlCl₃; CH₃COCl Step 3: NaOH + I₂ (or Cl₂) then H⁺ Step 4: LiAlH₄ (in dry ether)

Step 4

ii) Name the mechanism of step 2 and state the type of reaction in step 4.

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Answer

Mechanism of Step 2: Electrophilic (aromatic) substitution Type of reaction in Step 4: Reduction

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