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Date May 2019 Marks available 2 Reference code 19M.3.hl.TZ1.19
Level HL Paper 3 Time zone TZ1
Command term Deduce Question number 19 Adapted from N/A

Question

Aspirin can be obtained from salicylic acid.

Additional information can be obtained from the 1H NMR spectrum of aspirin.

Unreacted salicylic acid may be present as an impurity in aspirin and can be detected in the infrared (IR) spectrum.

Name the functional group and identify the absorption band that diff erentiates salicylic acid from aspirin. Use section 26 of the data booklet.

Name:

Absorption band:

[2]
a.

Deduce the protons responsible for signals X and Y by marking them on the structure of aspirin in (a). Use section 27 of the data booklet.

[2]
b(i).

Identify the splitting pattern of signals X and Y.

 

X:

Y:

[1]
b(ii).

Markscheme

Name:
hydroxyl   [✔]

Absorption band:
3200–3600 «cm–1»  [✔]

 

Note: Accept “phenol” OR “alcohol” but not “hydroxide”. 

a.

correct X   [✔]
correct Y   [✔]

 

Note: X and Y must be near the Hs.

b(i).

X: singlet AND Y: singlet  [✔]

b(ii).

Examiners report

Many candidates scored a mark for naming a functional group that differentiates salicylic acid from aspirin. Some incorrectly said ether or carboxylic acid. Many candidates also scored for identifying the absorption band although 1700-1750 was a popular incorrect answer.

a.

There was considerable confusion with indicating protons responsible for 1H NMR signals. Often entire functional groups were circled or carbon atoms and not hydrogen atoms were circled.

b(i).

There was also great difficulty in identifying the splitting pattern of the signals. It was rare to see both signals identified as singlets.

b(ii).

Syllabus sections

Options » B: Biochemistry » B.9 Biological pigments (HL only)
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