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

Carboxylic acids and derivatives — practice question

Fermenting sugars with bacteria or moulds yields many different organic compounds. One such compound found in fermented molasses is 2-ethyl-3-methylbutanoic acid, (CH$_3$)$_2$CHCH(C$_2$H$_5$)CO$_2$H, and this is what gives rum its characteristic aroma.
(a(i))[1]

What molecular formula does 2-ethyl-3-methylbutanoic acid have?

(a(ii))[1]

How many chiral carbon atoms are there in a molecule of 2-ethyl-3-methylbutanoic acid? If none, write 'none'.

(b(i))[2]

A sample of 2-ethyl-3-methylbutanoic acid can be made by oxidising 2-ethyl-3-methylbutan-1-ol, (CH$_3$)$_2$CHCH(C$_2$H$_5$)CH$_2$OH. State the reagent(s) needed for this oxidation and describe the colour change that would be seen.

(b(ii))[2]

This reaction is done by heating the reactants together. What could be the main organic impurity in the acid sample? Explain your answer.

(b(iii))[2]

State whether a distillation apparatus or a reflux apparatus should be used. Explain your answer.

(c)[3]

A structural isomer of 2-ethyl-3-methylbutan-1-ol is 2-ethyl-3-methylbutan-2-ol, $(\text{CH}_3)_2\text{CHC}(\text{OH})(\text{C}_2\text{H}_5)\text{CH}_3$. What colour change would be seen if this were heated with the reagents you have given in (b)(i)? Explain your answer as clearly as you can.

(d)[3]

An isomer of 2-ethyl-3-methylbutanoic acid which is an ethyl ester is a very strong smelling compound which is found in some wines. This ethyl ester has a branched hydrocarbon chain and is chiral. Draw the displayed formula of this ethyl ester. Identify the chiral carbon atom with an asterisk (*).

Worked solution & mark scheme

This 14-mark question has a full step-by-step worked solution and mark scheme. One marking point: Molecular formula correctly given as $\mathrm{C_7H_{14}O_2}$

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