Organic chemistry

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Question 26
Medium

Crude oil is separated into different fractions by fractional distillation.

Table 1 shows information about three of the hydrocarbon molecules found in three different fractions.

Table 1

MoleculeFormulaBoiling point (∘C^\circ\text{C}∘C)
hexaneC6H14\text{C}_{6}\text{H}_{14}C6​H14​69
tetradecaneC14H30\text{C}_{14}\text{H}_{30}C14​H30​254
octacosaneC28H58\text{C}_{28}\text{H}_{58}C28​H58​432
a.

Which of these three molecules would be separated highest up the fractionating column? Explain your answer using ideas about molecular size and boiling point.

[3]
b.

Cracking breaks down large hydrocarbons produced in fractional distillation into smaller, more useful molecules. The chemical equation shows the cracking of octadecane:

C18H38→C12H26+3C2H4 \text{C}_{18}\text{H}_{38} \rightarrow \text{C}_{12}\text{H}_{26} + 3\text{C}_2\text{H}_4 C18​H38​→C12​H26​+3C2​H4​ octadecane→dodecane+3×molecule Z \text{octadecane} \rightarrow \text{dodecane} + 3 \times \text{molecule }\mathbf{Z} octadecane→dodecane+3×molecule Z

State the name of molecule Z\mathbf{Z}Z, C2H4\text{C}_2\text{H}_4C2​H4​.

[1]
c.

Molecule Z\mathbf{Z}Z has the general formula CnH2n\text{C}_n\text{H}_{2n}Cn​H2n​. Octadecane and dodecane are both alkanes. State the general formula of the alkanes.

[1]
d.

Table 2 shows the percentage supply and percentage demand for some of the different fractions obtained from crude oil.

Table 2

FractionPercentage supply (%)Percentage demand (%)
LPG46
petrol928
naphtha128
kerosene14[blank]
diesel oil2227
fuel oil3921

Calculate the percentage demand for kerosene.

[2]
e.

Suggest why fuel oil, rather than diesel oil, is cracked to obtain petrol.

[2]

Organic chemistry Questions

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