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

Carboxylic acids and derivatives — practice question

Compound A contains only carbon, hydrogen and oxygen. When A is heated in aqueous sulfuric acid, compounds B and C are formed, as illustrated in Fig. 5.1. $\text{A} + 2\text{H}_2\text{O} \xrightarrow[\text{heat}]{\text{H}_2\text{SO}_4(aq)} \text{HOOCCH}_2\text{COOH} + 2\text{CH}_3\text{CH}_2\text{OH}$
(a)[2]

Draw the structure for A.

(b)[1]

Name the reaction type for heating A with aqueous $\text{H}_2\text{SO}_4$.

(c(i))[1]

Complete the equation that represents the reaction of B with excess aqueous sodium carbonate. $\ldots\text{HOOCCH}_2\text{COOH} + \ldots\text{Na}_2\text{CO}_3 \rightarrow \ldots$

(c(ii))[1]

Suggest why C does not react with aqueous sodium carbonate in a reaction similar to B.

(d(i))[2]

Identify the reagents and conditions needed in steps 1 and 2 to make B, as shown in Fig. 5.2. Step 1: $\text{ClCH}_2\text{CH}_2\text{CH}_2\text{Cl} \rightarrow \text{HOCH}_2\text{CH}_2\text{CH}_2\text{OH}$ Step 2: $\text{HOCH}_2\text{CH}_2\text{CH}_2\text{OH} \rightarrow \text{HOOCCH}_2\text{COOH}$

(d(ii))[1]

Identify the type of reaction that $\text{HOCH}_2\text{CH}_2\text{CH}_2\text{OH}$ undergoes in step 2.

(e(i))[1]

Identify the formula of the reducing agent R.

(e(ii))[2]

Complete the equation to show how B reacts with an excess of R. Use $[\text{H}]$ to represent one hydrogen atom from R. $\ldots\text{HOOCCH}_2\text{COOH} + \ldots[\text{H}] \rightarrow \ldots$

(e(iii))[1]

Name organic compound E.

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