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Limits of infrared evidence

Infrared shows which bonds a compound has but not where they are, how long the chain is, or the molecular mass; it rules candidates out, and matching group peaks shows consistency, not identity.

Paper packet. Every task here also exists on screen, where it is checked automatically; answers written on paper are not assessed by Nydus. When you are back at a device, enter your answers there.

1. What you will learn

You will sort questions IR can and cannot answer, decide which pairs IR can tell apart, name what IR cannot give, count the structures a spectrum leaves, and judge what a peak match proves.

2. What you already have

You can read which functional groups a spectrum shows. The other half of using evidence well is saying what it leaves open.

3. Words for this lesson

A candidate structure is one consistent with the evidence so far. Consistent with means not ruled out; it is weaker than identified as. The fingerprint region, below 1500 cm−1, is unique to each compound but hard to interpret by eye.

4. Bonds, not arrangement

Infrared sees bonds. So it cannot tell apart compounds that have the same bonds in different places:

What it does well is rule things out. For C3H8O the isomers are propan-1-ol, propan-2-ol and methoxyethane. A broad O–H band removes the ether and leaves two alcohols; no O–H band leaves only the ether.

Another way: steps

To use IR honestly:

  1. List every candidate the other evidence allows.
  2. Strike out those whose bonds the spectrum contradicts.
  3. State what is left, and what would decide between them.

5. Consistent is not identified

A spectrum that shows an O–H, a C=O and a benzene ring is consistent with aspirin and with dozens of other compounds. To identify a substance, a chemist matches its whole spectrum, fingerprint region included, against a reference, and usually adds other evidence: a mass spectrum for the molecular mass, NMR for which atoms are next to which. The next lessons add the mass spectrum and then combine the evidence.

6. Where this goes wrong

Every functional group has one exact IR frequency. Groups absorb over a range.

Matching peaks identifies a compound. It shows consistency.

IR tells where a group is on the chain. It shows the group, not its position.

IR gives the molecular mass. It gives none.

7. C4H10O with no O–H and no C=O

  1. Isomers of C4H10O: four alcohols and three ethers.

    List the candidates.

  2. No O–H rules out all four alcohols.

    Strike out what is contradicted.

  3. Three ethers remain, which IR alone cannot separate.

    Say what is left.

8. Your turn: C3H8O with no O–H band

  1. Which isomers have no O–H?

    Only methoxyethane.

  2. How many candidates remain?

  3. Your turn: work this step out. Its working is at the end of the packet.

    One: the compound is methoxyethane.

9. Guided practice

A chemist runs an infrared spectrum on an unknown liquid. Mark every question the spectrum alone can answer.

This task has no paper form; do it on a device.

10. Guided practice

Match each pair of compounds to whether infrared group peaks can tell them apart.

yes: one has a bond the other lacksno: same functional group, same group peaks
propanone and propan-2-ol
butan-1-ol and butan-2-ol
hexane and hex-1-ene

11. Practice

Which of these can an infrared spectrum not tell you about a pure compound?

12. Practice

A compound is C3H8O. Its IR spectrum shows a broad O–H band and no C=O. How many structures are still possible?

Answer:

13. Somewhere new

An analyst reports that a seized powder 'is aspirin' because its IR spectrum shows an O–H band, a C=O peak and aromatic peaks, all of which aspirin has. How strong is the claim?

14. Lesson test

Lesson test: one question per skill, one attempt each, no hints. Your answers are checked when you submit.

15. Test question

A compound is C3H8O. Its IR spectrum shows no O–H band and no C=O. How many structures are still possible?

The number of structures still possible is a.

16. What you can do now

You can say what an infrared spectrum leaves open. Tell someone why IR cannot tell butan-1-ol from butan-2-ol. Next: the mass spectrum, which gives the molecular mass IR cannot.

Working for the steps left to you

8. Your turn: C3H8O with no O–H band, step 3