Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

The amino acid serine, $\text{HOCH}_2\text{CH(NH}_2\text{)COOH}$, can occur in two optically active forms. These optical isomers, isomer P and isomer Q, are illustrated in Fig. 8.1.
(a)[1]

Isomer P and isomer Q have the same physical and chemical properties except for two specific features. One of these is the way they affect plane polarised light. State the other feature in which they differ.

(b)[1]

A pure solution of isomer P at a particular concentration rotates plane polarised light by $5.0^{\circ}$ in a clockwise direction. Describe how a pure solution of isomer Q of the same concentration affects plane polarised light.

(c)[1]

State another term, in addition to stereoisomers, optical isomers and non-superimposable mirror images, that can be used to describe this pair of chiral compounds, isomer P and isomer Q.

(d)[1]

Give the term used to describe a mixture containing equal amounts of isomer P and isomer Q.

(e)[1]

Describe one way in which a single optical isomer of serine can be produced, instead of making a mixture of isomer P and isomer Q.

(f)[3]

Complete Table 8.1 so as to describe the peaks observed in the proton ($^1\text{H}$) NMR spectrum of $\text{HOCH}_2\text{CH(NH}_2\text{)COOH}$ dissolved in $\text{D}_2\text{O}$. Use as many rows in Table 8.1 as necessary and leave any remaining rows blank.

(g)[1]

Proline is a naturally occurring amino acid. Its skeletal formula is shown. State the number of peaks in the carbon-13 ($^{13}\text{C}$) NMR spectrum of proline.

(h)[3]

Glutamic acid is a naturally occurring amino acid. Its skeletal formula is shown. The isoelectric point of glutamic acid is pH $3$. A sample of glutamic acid is dissolved in a solution of pH $1$. A strong alkali is then added until the pH of the mixture reaches pH $14$. As this happens, all possible ionised forms of glutamic acid are present at different times, depending on the pH of the solution. Complete the boxes below to show four different ionised forms of glutamic acid that are present at the stated pH values.

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