Chemistry 9701 · AS & A Level · Halogen compounds

Halogen compounds — practice question

Some reactions involving 1-bromobutane, $\text{CH}_3(\text{CH}_2)_3\text{Br}$, are shown.
(a)[6]

For each reaction shown, state the reagent(s), any particular conditions needed, and the reaction type. For the reaction type choose from the list: elimination, hydrolysis, substitution, oxidation, addition, condensation.

(b)[2]

Complete the diagram to show the $\text{S}_\text{N}2$ mechanism of reaction 1. $R$ represents the $\text{CH}_3(\text{CH}_2)_2$ group. Include all required charges, dipoles, lone pairs and curly arrows.

(c(i))[4]

Define the term structural isomer and name the three different types of structural isomerism.

(c(ii))[3]

2-bromo-2-methylpropane is treated with the same reagents as in reaction 1. Methylpropan-2-ol is formed. Identify the mechanism for this reaction. Explain why this reaction follows a different mechanism from reaction 1.

(d(i))[2]

Explain the meaning of the term stereoisomers.

(d(ii))[2]

Give two reasons why but-1-ene does not show stereoisomerism.

(d(iii))[2]

Name $X$ and $Y$.

(d(iv))[1]

Name the type of stereoisomerism shown by $X$.

(d(v))[2]

Use the conventional representation to draw the two stereoisomers of $X$.

Worked solution & mark scheme

This 24-mark question has a full step-by-step worked solution and mark scheme. One marking point: Aqueous / dilute NaOH or KOH (or water): substitution / hydrolysis

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