Alcohols

EasyMediumHard
1
Question 1
Hard

This question is about alcohols and related organic compounds.

a.

An unsaturated alcohol has 5 carbon atoms and contains one C=C\text{C}=\text{C}C=C bond.

Construct a balanced equation for the complete combustion of this alcohol.

[2]
b.

Compound E, shown below, is refluxed with excess acidified potassium dichromate(VI) to form a single organic product and one other product.

Complete the equation for this reaction by writing the structural formula or drawing the skeletal/displayed formula of the organic product, and balancing the equation.

Skeletal structure of Compound E: a five-carbon chain (pentane-1,2,4-triol derivative). Carbon-1 has a hydroxyl group (-OH) attached, making it a primary alcohol. Carbon-2 has a methyl group (-CH3) and a hydroxyl group (-OH) attached, making it a tertiary alcohol. Carbon-4 has a hydroxyl group (-OH) attached, making it a secondary alcohol. Thus, Compound E is 2-methylpentane-1,2,4-triol.

Compound E+……[O]⟶…⋯+……H2O\text{Compound E} + \dots\dots [\text{O}] \longrightarrow \dots\dots + \dots\dots \text{H}_2\text{O}Compound E+……[O]⟶…⋯+……H2​O

[3]
c.

Compound F, shown below, is refluxed with H2SO4\text{H}_2\text{SO}_4H2​SO4​, as an acid catalyst, to form a mixture of three isomers with the molecular formula C6H8\text{C}_6\text{H}_8C6​H8​.

Skeletal structure of Compound F: 1-methylcyclopentane-1,3-diol. A five-membered cyclopentane ring where Carbon-1 is bonded to a methyl group and a hydroxyl (-OH) group, and Carbon-3 is bonded to a hydroxyl group (-OH).

Draw or describe the structures of the three isomers of C6H8\text{C}_6\text{H}_8C6​H8​ formed from the double dehydration of compound F.

[3]
d.

A student converts compound F into a diiodoalkane. Suggest suitable reagents for this reaction.

[1]
e.

There are 3 structural isomers of C4H10O\text{C}_4\text{H}_{10}\text{O}C4​H10​O that are ethers.

A student predicts that these structural isomers could be distinguished using carbon-13 NMR spectroscopy.

Explain whether the student is correct.

In your answer, show how the peaks in the carbon-13 NMR spectra are linked to the structure of each ether isomer.

[4]

Alcohols Questions

  1. A Level
  2. /Chemistry
  3. /Alcohols