Cal 3 Nomenclature

Carboxylic Acid Suffix and Suffix Format

-oic acid (appended as -anoic acid after removing the 'e' from the alkane name)

Carboxylic Acid Prefix

carboxy-

Carboxylic Acid Root Chain Rule

Based on the longest continuous carbon chain containing the carboxylic acid group, with C1 assigned to the carbonyl carbon

Ester Suffix and Functional Class Name

Substituent suffix: -oate; Functional class name: alkyl alkanoate

Ester Alcohol Component Naming

Named first as an alkyl group based on the longest chain containing the OH group

Ester Carboxylic Acid Component Naming

Named second as an alkanoate based on the longest chain containing the carbonyl carbon (C1)

Amide Suffix and Functional Class Name

Substituent suffix: -amide; Functional class name: alkyl alkanamide

Amide Carbon Chain Rule

Root name is based on the longest continuous carbon chain containing the carbonyl carbon (assigned C1)

Amide Nitrogen Substituent Locant

Substituents on the amide nitrogen use N- as the locant (e.g., N-methyl or N,N-dimethyl)

Acyl Halide Suffix and Functional Class Name

Substituent suffix: -oyl halide; Functional class name: acyl halide or acid halide

Acyl Halide Chain Rule

Root name is based on the longest chain including the carbonyl group (assigned C1)

Acid Anhydride Suffix and Functional Class Name

Substituent suffix: -oic anhydride; Functional class name: alkanoic anhydride

Symmetric Acid Anhydride Naming

Named as alkanoic anhydride based on the carbon chain of the identical carboxylic acid units

Asymmetric Acid Anhydride Naming

Named by listing the two different carboxylic acid alkyl chain components in alphabetical order followed by anhydride

Cyclic Acid Anhydride Naming

Derived from dicarboxylic acids and named as -dioic anhydrides

Nitrile Suffixes and Prefix

Functional group suffixes: -nitrile or -onitrile; Functional class: alkyl cyanide; Substituent prefix: cyano-

Nitrile Suffix Style Chain Rule

Root name is based on the longest chain including the nitrile carbon (assigned C1)

Cyano Substituent Style Rule

The nitrile group is treated as a cyano- substituent on an alkane chain numbered to give the -C≡N group the lowest locant

Benzene Formula and Functional Class Name

Formula: C6H6; Functional class: arenes

Toluene Systemic and Common Name

Common name: Toluene; IUPAC name: Methylbenzene (C6H5CH3)[cite: 104].

Styrene Systemic and Common Name

Common name: Styrene; IUPAC name: Ethenylbenzene (C6H5CH=CH2)

Phenol Systemic and Common Name

Common name: Phenol; IUPAC name: Hydroxybenzene (C6H5OH)

Anisole Systemic and Common Name

Common name: Anisole; IUPAC name: Methoxybenzene (C6H5OCH3)[cite: 104].

Aniline Systemic and Common Name

Common name: Aniline; IUPAC name: Aminobenzene (C6H5NH2)[cite: 105].

Benzoic Acid Systemic and Common Name

Common name: Benzoic acid; Formula: C6H5CO2H[cite: 105].

Benzaldehyde Systemic and Common Name

Common name: Benzaldehyde; Formula: C6H5CHO[cite: 105].

Benzonitrile Systemic and Common Name

Common name: Benzonitrile; IUPAC name: Cyanobenzene (C6H5CN)[cite: 105].

Phenyl vs Benzyl Substituent Groups

Phenyl substituent = -C6H5; Benzyl substituent = -CH2C6H5[cite: 105, 106].

Disubstituted Benzene Locants: Ortho (o-)

1,2-disubstituted relative positions on a benzene ring[cite: 106].

Disubstituted Benzene Locants: Meta (m-)

1,3-disubstituted relative positions on a benzene ring[cite: 106].

Disubstituted Benzene Locants: Para (p-)

1,4-disubstituted relative positions on a benzene ring[cite: 106].

Polysubstituted Benzene Naming Rules

Numerical locants define positions for 3 or more substituents, with C1 assigned to the principal functional group and remaining substituents listed alphabetically[cite: 107].

Cahn-Ingold-Prelog (CIP) Priority Rule 1

At a stereocenter, assign priority based on atomic number; higher atomic number receives higher priority[cite: 108].

CIP Priority First Point of Difference Rule

If attached atoms are identical, compare the atoms attached to them moving outward one bond at a time until the first point of difference is found[cite: 108, 109].

CIP Priority Multiple Bond Treatment

Multiple bonds are treated as an equivalent number of single bonds (e.g., C=O is treated as C attached to two O atoms)[cite: 108, 109].

CIP Priority Isotope Rule

Isotopes with identical atomic numbers are prioritized by mass number (e.g., Deuterium > Hydrogen)[cite: 108, 109].

E / Z Alkene Nomenclature Definition

Z isomer has higher priority groups on the same side of the double bond; E isomer has higher priority groups on opposite sides[cite: 108].

Chirality Center Definition

An sp3 hybridized atom (most commonly carbon) bonded to four different groups resulting in non-superimposable mirror images[cite: 108].

R / S Stereocenter Configuration Rule

With the lowest priority group (4) pointed away from the viewer along the C-4 bond, a 1 -> 2 -> 3 priority direction that is clockwise is R and counterclockwise is S[cite: 109].

Common Student Error in Assigning R/S

Failing to position the lowest priority group (group 4) pointing away from the viewer before determining clockwise vs counterclockwise rotation[cite: 109].

common substituent benzene name

toluene

common substituent benzene name

styrene

common substituent benzene name

phenol

common substituent benzene name

anisole

common substituent benzene name

aniline

common substituent benzene name

benzoic acid

common substituent benzene name

benzaldehyde

common substituent benzene name

benzonitrile

butanoic acid

methyl propanoate

isopropyl propanoate

methyl-2-methylpropanoate

isopropyl-2-methylbutanoate

butanamide

N-methylbutanamide

N,N-dimethylethanamide

ethanoyl chloride

butanoyl chloride

2-methylpropanoyl chloride

ethanoic anhydride

butanoic propanoic anhydride

pentandioic anhydride

Cyano substituent style

1-cyanopropane

nitrile style

butanenitrile

ethylbenzene

bromobenzene

ethoxybenzene

nitrobenzene

phenylethene

3-phenylpropene

2-phenylethanol

phenyl or benzyl?

phenyl bromide

phenyl or benzyl?

benzyl bromide

phenyl or benzyl?

ethyl phenyl ether

phenyl or benzyl?

benzyl methyl ether

Numerical locants method

1,2-dichlorobenzene

Ortho / Meta/ para Method 

ortho-dichlorobenzene

Numerical locants method

1-bromo-2-chlorobenzane

Ortho / Meta/ para Method 

meta-bromochlorobenzene

Numerical locants method

2-chlorophenol

Ortho / Meta/ para Method 

ortho-chlorophenol

2-bromo-4-chlorotoluene

3,5-dimethylphenol

2-ethyl-3-methylaniline

What functional group is this?

carboxylic acid

What functional group is this?

ester

What functional group is this?

amide

What functional group is this?

acyl halide

What functional group is this?

Acid Anhydride

What functional group is this?

nitrile

What functional group is this?

benzene