OCR A-Level Chemistry Synthesis and analytical techniques (02), June 2022: Question 11

1 mark · Medium difficulty · Multiple Choice

Identify the organic compound that produced the given infrared spectrum from four multiple-choice options.

Practise this question

Question

An infrared spectrum showing transmittance percentage on the vertical axis from 0 to 100 and wavenumber in reciprocal centimeters on the horizontal axis from 4000 to 500. There is a strong, deep absorption peak around 1740 cm^-1 corresponding to a C=O bond, and no broad absorption around 3200-3600 cm^-1 for an O-H bond. Below the spectrum are four multiple-choice options: A, H2C=CHCH2CH2OH; B, CH3COOCH2CH3; C, H2NCH2COOCH3; and D, (CH3)2CHCONH2.
Question text

11 The infrared spectrum of an organic compound is shown below.

Transmittance (%)

4000 3000 2000 1500 1000 500

Wavenumber / cm–1

Which compound could have produced this spectrum?

A H2C=CHCH2CH2OH

B CH3COOCH2CH3

C H2NCH2COOCH3

D (CH3)2CHCONH2

Your answer

[1]

Mark scheme

Show the mark scheme The mark scheme indicates the correct answer is B for question 11, worth 1 mark.

11 B 1 AO2.5

How to answer it

Analysing an Infrared (IR) Spectrum

What this question tests

This question tests your ability to interpret infrared (IR) spectra using absorption wavenumber data from the Data Sheet, linking specific characteristic peaks (such as C=O and C-H stretches) to functional groups present in organic molecules.

Question 11

Identifying the Organic Compound from its IR Spectrum

✅ Correct Answer

B ( CH₃COOCH₂CH₃ )

Mark Awarded: 1 / 1 (AO2.5)

💡 Key Knowledge

  • C=O Stretch: A very strong, sharp dip around 1680–1750 cm⁻¹ indicates a carbonyl group. Here, a deep absorption peak is clearly visible around 1740 cm⁻¹.
  • Absence of O-H: There is no broad absorption peak in the 3200–3600 cm⁻¹ region, ruling out alcohols and carboxylic acids.
  • C-H Stretch: Strong absorptions just below 3000 cm⁻¹ indicate aliphatic C-H stretching.

🧠 Exam Technique

  • Elimination Strategy: Scan for major diagnostic peaks first. The sharp peak at ~1740 cm⁻¹ instantly confirms a C=O bond, eliminating compound A (which has an O-H stretch instead).
  • Check Remaining Options: Options B, C, and D all contain carbonyl or similar functional groups, so look closer at the specific structure and other regions (like C-O stretches around 1000–1300 cm⁻¹ found in esters).

❌ Common Errors

  • Confusing the sharp C-H aliphatic stretch (just below 3000 cm⁻¹) with a broad O-H alcohol stretch (which appears at higher wavenumbers, 3200–3600 cm⁻²).
  • Failing to check the Data Sheet absorption values, leading to misidentification of the strong 1740 cm⁻¹ peak.

Topics

Module 6: Organic chemistry and analysis · Module 4: Core organic chemistry · 6.3 Analysis · 4.2 Alcohols, haloalkanes and analysis

Question and mark scheme from the OCR A-Level Chemistry examination, Synthesis and analytical techniques (02), June 2022. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.