Chemistry 9701 · AS & A Level · Halogen compounds

Halogen compounds — practice question

Several reactions are depicted, all of which are based on methylpropan-2-ol, $(\text{CH}_3)_3\text{COH}$.
(a)[5]

For each reaction, give the reagent(s), any specific conditions needed, and the reaction type. For the reaction type, select from: hydrolysis, dehydration, substitution, oxidation, addition, condensation. Any type may be used once, more than once, or not at all. A single reaction may be described by one type or by more than one type.

(b)[3]

Draw a diagram that shows the $\text{S}_\text{N}1$ mechanism for reaction 2. Include every necessary charge, dipole, lone pair and curly arrow.

(c(i))[4]

1-bromobutane is a structural isomer of the product of reaction 1. Define structural isomer and name the three distinct types of structural isomerism.

(c(ii))[3]

1-bromobutane is reacted with the same reagents as in reaction 2. Butan-1-ol is produced. Identify the mechanism of this reaction. Explain why this reaction follows a different mechanism from reaction 2.

(d(i))[2]

The product of reaction 3, methylpropene, does not display stereoisomerism. Give two reasons why methylpropene does not display stereoisomerism.

(d(ii))[3]

Methylpropene can be polymerised to make a poly(alkene). State the type of polymerisation and draw the repeat unit of the polymer made from methylpropene.

(d(iii))[1]

State the disposal problem associated with poly(alkenes).

(e)[2]

Name the two products from reaction 4. Name of $(\text{CH}_3)_3\text{CBr}$. Name of $(\text{CH}_3)_2\text{CHCH}_2\text{Br}$.

(ii)[3]

Methylpropene can be polymerised to form a poly(alkene). State the type of polymerisation and draw the repeat unit of the polymer made from methylpropene. Type of polymerisation: Repeat unit:

(iii)[1]

State the disposal problem associated with poly(alkenes).

Worked solution & mark scheme

This 27-mark question has a full step-by-step worked solution and mark scheme. One marking point: Application of concentrated $\text{H}_2\text{SO}_4$ / $\text{H}_3\text{PO}_4$ with $\text{NaBr}$, or red P / $\text{Br}_2$, or $\text{HBr}$

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