Carboxylic acids and derivatives — Chemistry 9701 AS & A Level Question & Worked Solution

(a(i))

Draw circles around the chiral centres in the structure above.

(a(ii))

Give the molecular formula of chlorogenic acid.

(a(iii))

How many moles of $\text{H}_2(\text{g})$ are released when $1$ mol of chlorogenic acid reacts with excess sodium metal?

(a(iv))

How many moles of $\text{NaOH}(\text{aq})$ react with $1$ mol of chlorogenic acid under each of the following conditions? In the cold. On heating.

(b(i))

What type of reaction is occurring when chlorogenic acid forms D and E?

(b(ii))

If the test with cold dilute acidified $\text{KMnO}_4$ had been positive, which functional group would that have indicated in F?

(b(iii))

Name the functional groups in compound F that would react with each of the following: $\text{Na}_2\text{CO}_3(\text{aq})$, $\text{Br}_2(\text{aq})$.

(b(iv))

Suggest structures for compounds F and G and draw them in the relevant boxes above.

(b(v))

Compound E is one member of a pair of stereoisomers. What type of stereoisomerism does compound E show?

(b(vi))[8]

Draw the structure of the other stereoisomer in the box below.

(c)[3]

Calculate the volume of $0.1\ \text{mol dm}^{-3}\ \text{NaOH}$ needed for complete reaction with $0.1\ \text{g}$ of compound E.

Carboxylic acids and derivatives — practice question