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CAIE A-Level Chemistry 29 Introduction to A-Level Organic Chemistry

Practise the functional-group, structural and reaction conventions needed for advanced organic chemistry questions.

Syllabus
2028–2030
Course
Chemistry 9701
Level
A2

Covered syllabus points

A Level organic chemistry conventions and functional group reference29.1 Formulas, functional groups and nomenclature29.2 Characteristic organic reactions29.3 Shapes of aromatic organic molecules; σ and π bonds29.4 Optical isomerism

29. An introduction to A Level organic chemistry question 1

[Maximum number: 1]

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

Name all the functional groups present in procaine.

29. An introduction to A Level organic chemistry question 2

[Maximum number: 2]

Cumene is an aromatic hydrocarbon used in the synthesis of other useful chemicals.

cumene

cumene

Question (a)

(a)

Complete Table 5.1 to show the number of sp2\mathrm{sp}^{2} and sp3\mathrm{sp}^{3} hybridised carbon atoms that are present in a molecule of cumene.

Table 5.1

Table 5.1

[ 1 ]

Question (b)

(b)

Cumene can be synthesised via a Friedel-Crafts alkylation reaction, as shown in Fig. 5.2.

Fig. 5.2

Fig. 5.2

[ 1 ]

Question (i)

(i)

Name the mechanism involved in the Friedel-Crafts alkylation shown in Fig. 5.2.

[ 1 ]

29. An introduction to A Level organic chemistry question 3

[Maximum number: 4]

The amino acid serine, HOCH2CH(NH2)COOH\mathrm{HOCH}_{2} \mathrm{CH}\left(\mathrm{NH}_{2}\right) \mathrm{COOH}, exists in two optically active forms. These optical isomers, isomer P and isomer Q, are shown in Fig. 8.1.

Fig. 8.1

Fig. 8.1

Question (a)

(a)

Isomer P and isomer Q have identical physical and chemical properties, with the exception of two specific properties. One of these two properties is their differing effect on plane polarised light.

State the other property by which they differ.

[ 1 ]

Question (b)

(b)

A solution of pure isomer P of a particular concentration rotates plane polarised light by 5.0∘5.0^{\circ} in a clockwise direction.

Describe how a solution of pure isomer Q of the same concentration affects plane polarised light.

[ 1 ]

Question (c)

(c)

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

[ 1 ]

Question (d)

(d)

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

[ 1 ]
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