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Functional-group names

A name is stem, locant and a suffix for the principal functional group, with every other group as a prefix; the group's own carbon counts in the chain, and esters are named as two words.

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 give each group's suffix, sort formulas into classes, name chains that end in a group, combine a suffix and a prefix, name an ester, and place a ketone's locant.

2. What you already have

You can name an alkane and know which group outranks which. A functional group's name replaces or adds to the alkane's -ane.

3. Words for this lesson

The principal group is the highest-priority group; it gives the suffix. Other groups are prefixes: hydroxy- (–OH), amino- (–NH2), oxo- (=O), chloro-. An ester R–COO–R′ is named as two words: the R′ group, then the acid part ending -oate.

4. Stem, locant, suffix

Take ethane's two carbons and change one group:

GroupSuffixExample
alcohol –OH-olethanol, CH3CH2OH
aldehyde –CHO-alethanal, CH3CHO
ketone C=O-onepropanone, CH3COCH3
carboxylic acid –COOH-oic acidethanoic acid, CH3COOH
amine –NH2-amineethanamine, CH3CH2NH2
nitrile –C≡N-nitrileethanenitrile, CH3CN
amide –CONH2-amideethanamide, CH3CONH2

The group's own carbon counts in the chain: ethanal has two carbons, one of them the CHO. A group that can sit in more than one place takes a locant, placed just before the suffix: propan-1-ol, propan-2-ol; pentan-2-one, pentan-3-one. Aldehydes and acids are always on carbon 1, so they need none.

Another way: steps

To name a chain with a group:

  1. Choose the parent chain through the principal group.
  2. Number from the end nearer that group.
  3. Stem + locant + suffix.
  4. Any other groups as numbered prefixes, alphabetically.

5. Prefixes, and esters

When a molecule has two groups, only the principal group is a suffix. HOCH2CH2COOH is 3-hydroxypropanoic acid: the acid names it, and the –OH becomes hydroxy- with its number. A name never has two principal suffixes.

Esters are the exception to one-word names. They are made from an acid and an alcohol, and named in that spirit: the group from the alcohol, then the acid's name with -oic acid changed to -oate. CH3COOCH3 is methyl ethanoate; the banana-smelling CH3COOCH2CH2CH2CH2CH3 is pentyl ethanoate.

6. Where this goes wrong

A functional group changes only the molecule's spelling. It changes the chemistry; the name records it.

The group's carbon is extra. It counts in the chain.

A molecule can have two suffixes. Only the principal group does.

Esters are one word. They are named as two.

7. CH3CH2CH2CH2OH

  1. Four carbons including the one with –OH: stem but-.

    Count the group's carbon.

  2. Number from the –OH end: it is on carbon 1.

    Nearest end.

  3. Put together, the name is butan-1-ol.

    Stem, locant, suffix.

8. Your turn: CH3CH2COOH

  1. How many carbons, counting the COOH carbon?

    Three: stem prop-.

  2. What ending does an acid take, and does it need a number?

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

    -anoic acid, no number: propanoic acid.

9. Guided practice

When an amide, –CONH2 is the highest-priority group in a molecule, what suffix ends the name?

The suffix is x.

10. Guided practice

Match each formula to the class of compound it is.

alcoholaldehydeketonecarboxylic acidester
CH3CH2OH
CH3CH2CHO
CH3COCH3
CH3CH2COOH
CH3COOCH3

11. Practice

An unbranched chain of $6$ carbon atoms, counting the group's own carbon, ends in a carboxylic acid group, –COOH. What is the compound's name?

The compound is n.

12. Practice

HOCH2CH2COOH has an alcohol group and a carboxylic acid group on a three-carbon chain. Which name is correct?

13. Somewhere new

The smell of bananas comes largely from the ester CH3COOCH2CH2CH2CH2CH3. What is its name?

It is n.

14. Lesson test

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

15. Test question

Name the ketone CH3CH2COCH2CH2CH3.

The ketone is n.

16. What you can do now

You can name a molecule by its principal group. Tell someone why HOCH2CH2COOH is an acid first and an alcohol second. Next: names that carry shape — E, Z, R and S.

Working for the steps left to you

8. Your turn: CH3CH2COOH, step 3