Chemistry 9701 · AS & A Level · Analytical techniques

Analytical techniques — practice question

Acetoin, $\text{CH}_3\text{COCH(OH)CH}_3$, and diacetyl, $\text{CH}_3\text{COCOCH}_3$, are two compounds responsible for butter’s distinctive flavour. Their skeletal formulae are shown.
(a)[1]

Give the IUPAC systematic name of acetoin.

(b)[2]

Identify the reagents and conditions needed to convert acetoin into diacetyl.

(c)

An infra-red spectrum of acetoin is shown.

(c(i))[3]

Explain the main features of this spectrum, referring to the peaks with wavenumbers above $1500\,\text{cm}^{-1}$.

(c(ii))[2]

State and explain how the infra-red spectrum of diacetyl would be different from the infra-red spectrum of acetoin.

(d)

If a sample of acetoin is reacted with concentrated sulfuric acid, one product is formed that does not show stereoisomerism. However, if a sample of acetoin is reacted with HBr, a mixture of a pair of stereoisomers is produced.

(d(i))[1]

Give the structural formula of the product formed when acetoin reacts with concentrated sulfuric acid.

(d(ii))[2]

Explain why the product in (i) does not show stereoisomerism.

(d(iii))[1]

Explain why the product of the reaction of acetoin with HBr does show stereoisomerism.

(d(iv))[2]

Draw the two stereoisomers from (iii) using the conventional representation.

Worked solution & mark scheme

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