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Names as structure checks

A valid name survives the round trip — draw it, name the drawing, get the same name back; names also give formulas, which say whether two compounds are the same, isomers, or different.

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 correct faulty names by the round trip, count atoms from a name, spot invalid names, and decide whether two named compounds are the same, isomers, or different.

2. What you already have

You can name a molecule from its structure. This lesson runs the process backwards, and then both ways round, as a check.

3. Words for this lesson

The round trip is drawing a structure from a name, then naming the drawing again: a valid name returns unchanged. Connectivity is which atoms are joined to which. Structural isomers share a molecular formula and differ in connectivity.

4. Draw it, name it again

A name is a set of instructions. 2-ethylbutane says: four carbons in a row, an ethyl group on carbon 2. Draw that — CH3CH(CH2CH3)CH2CH3 — and name it from scratch. The longest chain runs through the ethyl group: five carbons, with a methyl on carbon 3. The drawing is 3-methylpentane, so '2-ethylbutane' failed the round trip.

The common failures:

Another way: steps

To check a name:

  1. Draw exactly what it says.
  2. Find the true longest chain in the drawing.
  3. Number from the nearer end.
  4. Rename. If the name changed, the original was wrong.

5. Counting atoms and comparing compounds

A name gives the formula too. 3-ethyl-2-methylhexane has six parent carbons plus two plus one, nine in all, and as an alkane C9H20. That makes names a quick way to compare compounds: if two names give the same structure, they are the same compound; if they give the same formula and a different structure, the compounds are isomers with different properties; if the formulas differ, they are simply different compounds. Butan-1-ol boils at 118 °C and its isomer 2-methylpropan-2-ol at 82 °C: same formula, different substances.

6. Where this goes wrong

Two names that sound similar must describe the same connectivity. Draw them and see.

The same formula means the same compound. Isomers share formulas.

A name is correct if it can be drawn. It must also be the name that drawing would get.

Branch carbons don't count in the formula. Every carbon counts.

7. Checking '1-methylbutane'

  1. Draw a four-carbon chain with CH3 on carbon 1: CH3CH2CH2CH2CH3.

    Exactly what it says.

  2. The longest chain is now five carbons with no branch at all.

    Find the true chain.

  3. The drawing is pentane, so '1-methylbutane' fails the round trip.

    Rename and compare.

8. Your turn: check '3-methylbutane'

  1. Draw it: four carbons, a methyl on carbon 3.

    CH3CH2CH(CH3)CH3.

  2. Number from the other end. Where is the methyl now?

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

    On carbon 2: it is 2-methylbutane.

9. Guided practice

A student names a compound 4-methylhexane. Draw the structure that name describes, then give its correct name.

The correct name is n.

10. Guided practice

How many carbon atoms are in 3-ethyl-2-methylpentane?

Answer:

11. Practice

Match each pair of names to how the compounds they describe are related.

the same compoundstructural isomers: same formula, different connectionsdifferent compounds with different formulas
pentane and 2,2-dimethylpropane
butan-1-ol and butan-2-ol
propane and propene
2-methylbutane and CH3CH(CH3)CH2CH3

12. Practice

A worksheet lists four names. Mark every name that cannot be correct as written.

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

13. Somewhere new

Two bottles in a store are labelled butan-1-ol and 2-methylpropan-2-ol. A technician says they must hold the same substance because both are C4H10O. Is that right?

14. Lesson test

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

15. Test question

How many hydrogen atoms does one molecule of 3-ethylpentane contain?

One molecule contains a hydrogen atoms.

16. What you can do now

You can use a name to test a structure. Tell someone why 2-ethylbutane is not a correct name. Next unit: what happens when a molecule rotates about its single bonds.

Working for the steps left to you

8. Your turn: check '3-methylbutane', step 3