Organic Chemistry IUPAC Nomenclature: Functional Groups and Naming

Rank the functional groups from highest to lowest priority.

Cation/anion salts > carboxylic acids > acid anhydrides > esters > acid halides > amides > nitriles > aldehydes > ketones > alcohols/thiols > amines > unsaturation > other groups (alkyl, alkoxy, alkylthio, halo, nitro).

What is a 1-carbon branch called?

Methyl

What is a 2-carbon branch called?

Ethyl

What is a 3-carbon branch called?

Propyl

What do di-, tri-, and tetra- mean?

Two, three, and four identical substituents.

Do di-, tri-, and tetra- count when alphabetizing branches?

No. Alphabetize by the branch name itself.

How do you alphabetize sec-butyl and tert-butyl?

Ignore sec- and tert- when alphabetizing.

How do you alphabetize isobutyl?

Include iso when alphabetizing.

What punctuation separates numbers from numbers in an IUPAC name?

Commas.

What punctuation separates numbers from words in an IUPAC name?

Hyphens.

What does the parent name tell you?

The number of carbons, unsaturation, and the highest-priority suffix.

What suffix identifies an aldehyde?

-al

What suffix identifies a ketone?

-one

What suffix identifies an alcohol?

-ol

What suffix identifies a compound with two alcohol groups?

-diol

What suffix identifies a compound with three alcohol groups?

-triol

What suffix identifies a thiol when no higher-priority group is present?

-ethiol

What must the parent chain include when naming an aldehyde?

The aldehyde carbonyl carbon.

How is the aldehyde carbon numbered?

It is carbon 1.

How is an aldehyde named from its parent alkane?

Replace the final -e with -al.

How is a ketone named from its parent alkane?

Replace the final -e with -one.

When naming a ketone, how do you number the chain?

Give the carbonyl carbon the lowest possible number.

What is the correct suffix for a ketone with its carbonyl at carbon 2 in a six-carbon chain?

hexan-2-one (also written 2-hexanone).

How is an aldehyde attached directly to a ring named?

As a carbaldehyde.

What suffix identifies a monocarboxylic acid?

-oic acid

What number is assigned to the carboxylic acid carbon?

Carbon 1.

How is a carboxylic acid attached to a ring named?

As a cycloalkane carboxylic acid.

What suffix identifies a dicarboxylic acid?

-dioic acid

What is the name of HOOC-(CH2)7-COOH?

Nonanedioic acid.

How do you name an acid halide?

Replace -ic acid with -yl halide.

How is an acid halide attached to a ring named in the slides?

Replace "carboxylic acid" with "carbonyl halide."

How are acid anhydrides named?

Replace "acid" with "anhydride."

How are asymmetrical acid anhydrides named?

List the two acid names alphabetically, followed by "anhydride."

How are esters named?

Name the alkyl group attached to oxygen first, then the acid portion ending in -ate.

What part of an ester name comes first?

The alkyl group attached to the single-bonded oxygen.

What suffix is used for the acid portion of an ester name?

-ate

What suffix identifies an amide?

-amide

How do you name an amide from the corresponding carboxylic acid?

Replace -ic acid or -oic acid with -amide.

How are alkyl groups attached to an amide nitrogen named?

Use N- before the substituent name, such as N-methyl.

What suffix identifies a nitrile?

-nitrile

What ending do carboxylate ions have?

-oate.

Name CH3CH2CHO.

Propanal.

Name CH3COCH3.

Propanone (acetone is its common name).

Name CH3CH2CH2CHO.

Butanal.

Name CH3COCH2CH3.

Butan-2-one (also written 2-butanone).

Name CH3CH2CH2COOH.

Butanoic acid.

Name HOOC-CH2-COOH.

Propanedioic acid.

Name CH3CH2COOCH3.

Methyl propanoate.

Name CH3COOCH2CH3.

Ethyl ethanoate.

Name CH3CH2CONH2.

Propanamide.

Name CH3CH2CN.

Propanenitrile.

What is the correct name for a five-carbon parent with two methyl groups both on carbon 2?

2,2-dimethylpentane.

When a ketone is part of a longer chain, what suffix is used if it is the principal group?

-one

What is the general format for a name with branches?

Locants and branch names in alphabetical order, followed by the parent name and suffix.