There are four alcohols, A, B, C and D, which are structural isomers and have the molecular formula $\text{C}_4\text{H}_{10}\text{O}$. Alcohol A does not react with acidified potassium dichromate(VI) solution, whereas B, C and D do react. When all four alcohols are heated with concentrated sulfuric acid, they form products with the molecular formula $\text{C}_4\text{H}_8$. A, C and D each produce only one product in this reaction. B gives a mixture of two structural isomers, one of which displays stereoisomerism.
(a)[7]
Give the skeletal formula for each of the four alcohols, and finish the diagram by naming the kinds of structural isomerism shown by each linked pair of compounds.
(b(i))[2]
Give the names of the two structural isomers formed when B reacts with hot, concentrated sulfuric acid.
(b(ii))[2]
State which of these two isomers shows stereoisomerism. Explain why this molecule is able to show stereoisomerism.
(b(iii))[2]
Draw displayed formulae to represent the two stereoisomers.
Worked solution & mark scheme
This 13-mark question has a full step-by-step worked solution and mark scheme. One marking point: “all four alcohol structures are correct” …