Chemistry 9701 · AS & A Level · Carboxylic acids and derivatives

Carboxylic acids and derivatives — practice question

A sequence of reactions is displayed.
(a)[2]

Complete the diagram so that the mechanism for reaction 1 is shown. Include every required charge, partial charge, lone pair and curly arrow.

(b(i))[1]

State the name of the reaction type in reaction 3.

(b(ii))[2]

Describe and explain how the infra-red spectrum of $W$ differs from that of propanoic acid.

(c(i))[2]

Reactions 4 and 5 use the same reagent. Give the reagent and the conditions required for reaction 4.

(c(ii))[1]

Give the conditions required for reaction 5.

(d(i))[1]

Under suitable conditions, ethanol and propanoic acid undergo a condensation reaction. State the condition needed for the reaction.

(d(ii))[1]

Draw the skeletal formula for the organic product of this reaction.

(d(iii))[1]

Give the name of the organic product of this reaction.

(e(i))[2]

Depending on the conditions shown, V reacts with acidified manganate(VII) ions in two different ways. Hot, concentrated $\text{MnO}_4^-/\text{H}^+$ produces propanoic acid as the only organic product, whereas cold, dilute $\text{MnO}_4^-/\text{H}^+$ gives T, which has two chiral centres. V decolourises bromine water. Give the structural formulae of V and T.

(e(ii))[2]

Identify the types of stereoisomerism displayed by V and T.

Worked solution & mark scheme

This 15-mark question has a full step-by-step worked solution and mark scheme. One marking point: Lone pair on C of $\mathrm{CN^-}$, with a curly arrow to C of C-Br

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