Prenol may be produced by reacting $G$ with $\text{NaOH}(aq)$. Complete the diagram to show the mechanism for the reaction between $G$ and $\text{NaOH}(aq)$ that produces prenol. Show all relevant charges, partial charges, lone pairs and curly arrows.
Prenol reacts with steam to give a mixture of three isomers, $J$, $K$ and $L$, with molecular formula $\text{C}_5\text{H}_{12}\text{O}_2$. When $J$ is heated with excess acidified potassium dichromate(VI) it produces an organic product that gives no reaction with 2,4-DNPH. Draw the structure of $J$.
Give the structural formula of K and L.
Name the type of stereoisomerism shown by K and L.
Give the balanced equation to represent the reaction of K, $\text{C}_5\text{H}_{12}\text{O}_2$, with acidified potassium dichromate(VI) to form M, $\text{C}_5\text{H}_8\text{O}_3$. Use [O] to represent an atom of oxygen supplied by the oxidising agent.
Prenol contains an alkene functional group. Describe a chemical test to confirm the presence of an alkene functional group. Give the result of the test.
Prenol can be polymerised to form poly(prenol). Draw one repeat unit of poly(prenol).
Give the name of N.
Isoprenol is a liquid. Ni acts as a catalyst for reaction 1. Identify the type of catalysis shown by Ni in reaction 1.
Draw the skeletal formula of Q and suggest one commercial use of Q.
The progress of reaction I can be followed using infra-red spectroscopy. One absorption that can be used to monitor the progress of this reaction is that of $\text{C-Cl}$ at $730\ \text{cm}^{-1}$. Identify another absorption that can be used to monitor the progress of this reaction. In your answer, you should refer to the specific bond and its corresponding absorption range in wavenumbers.
State the reagent(s) needed for reaction II.
Name the type of reaction that occurs in reaction III.
The yield of reaction I is very low. Explain why.
P can be produced as shown.