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CAIE A-Level Chemistry A2 36 Organic Synthesis Questions

Practise identifying functional groups, planning multi-step routes and analysing reagents, products and by-products, checking each transformation against structures and reaction…

Syllabus
2028–2030
Course
Chemistry 9701
Level
A2

Covered syllabus points

36.1 Organic synthesis

Question 1

[Maximum number: 2]

Asparagine and aspartic acid are two naturally occurring amino acids. Their structures and isoelectric points are shown in Table 8.1.

Table 8.1

Table 8.1

Asparagine and aspartic acid are treated separately with an excess of LiAlH4\mathrm{LiAlH}_{4}.

Draw the structures of the organic products of these reactions.
product of asparagine treated with an excess of LiAlH4\mathrm{LiAlH}_{4}
product of aspartic acid treated with an excess of LiAlH4\mathrm{LiAlH}_{4}

Question 2

[Maximum number: 3]

Procaine is used as an anaesthetic in medicine. It can be synthesised from methylbenzene in five steps as shown in Fig. 7.1.

Fig. 7.1

Fig. 7.1

Procaine is synthesised in three steps from X.

Suggest the reagents and conditions for step 4 and for step 5 in Fig. 7.1.
step 4
step 5

Question 3

[Maximum number: 5]

Question (a)

(a)

3-aminobenzoic acid can be synthesised from methylbenzene in three steps. methylbenzene

Figure for Question (a) — CAIE A-Level Chemistry A2
[ 5 ]

Question (i)

(i)

Draw the structures of M and N in the boxes.

[ 2 ]

Question (ii)

(ii)

Suggest reagents and conditions for each step of the synthesis. step 1
step 2
step 3

[ 3 ]

Question 4

[Maximum number: 3]

The ester 4-methylphenyl benzoate is used in the manufacture of perfumes.

4-methylphenyl benzoate

4-methylphenyl benzoate

Suggest a two-step route for the synthesis of 4-methylphenyl benzoate from 4-methylphenol and benzoic acid.
Include reagents and conditions for each step, and the structure of the intermediate compound.

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