Substituents/functional groups and nomenclature

List carbonyl functional groups

Ketones, aldehydes, carboxylic acids, ester, amides

List hydrocarbon functional groups

Alkanes, alkenes, alkynes

List simple oxygen functional groups

Alcohols, ethers

How to identify alkanes

Single carbon-carbon bond (C-C)

How to identify alkenes

Double carbon-carbon bonds (C=C)

How to identify alkynes

Triple carbon-carbon bonds

How to identify alcohols

Contains hydroxyl group (-OH) bonded to carbon

How to identify ethers

Oxygen atom bonded between two carbon chains (R-O-R)

How to identify ketones

Carbonyl carbon (C=O) sits between two carbon (R) groups

How to identify aldehydes

Carbonyl group (C=O) is attached to a hydroxide (-CHO) group at end

How to identify carboxylic acid

How to identify ester group

Carbonyl group (C=O) directly bonded to a second, single-bonded oxygen atom that continues into another carbon chain. Generally -C(=O)-O-C

How to identify amides

Carbonyl (C=O) attached to a nitrogen

What is a carbonyl?

C=O

How to identify an amine

Contains a nitrogen atom single bonded to carbons R3N. Either has lone pair or hydrogen as fourth bond.

How to identify alkyl halides

Carbon bonded to halogen R-X, X=F, Cl, Br, I

How to identify an aryl group

Flat, ring-shaped carbon structure with alternating double bonds connected to larger molecule. Has hydrogen removed. Ar-

How to identify sulfide/thioether

R-S-R'

Thiol

R-SH

Functional group of an alkyl halide

Halo group

Functional group of an alcohol

Hydroxy group

Functional group of an ether

-OR alkoxy group

Functional group of a thiol

Mercapto group

Functional group of a sulfide

-SR alkythio group

Hydroxyl + carbon + aromatic hydrocarbon

Aromatic alcohol

Aromatic hydrocarbon w 1+ benzene ring

Arene

Carbon-nitrogen triple bond

Nitrile

Two acyl groups with a common central oxygen (RCO)2O

Acid anhydride

Carbonyl + chlorine, R-COCl

Acyl/acid chloride

Carbonyl + nitrogen R-C(=O)-NH2

Amide

Hydrogen in hydroxyl replaced by organyl RCOOR'. Derived from acid, organykl from alcohol

Ester

R-COOH

Carboxylic acid

Carbonyl inside carbon chain/ring

Ketone

Carbonyl + hydrogen. -CHO

Aldehyde

R-S-R'

Sulfide

R-SH

Thiol

R-NH2, R2NH, R3N

Amine

R-O-R'

Ether

R-OH

alcohol

R-X

alkyl halide

Two carbonyls w a central oxygen -C(=O)-O-C(=O)

Anhydride

Carbonyl group + halogen

Acid halide

Halogen bonded to sp²-hybridized alkene carbon (R-CH=CH-X). Low reactivity

Vinyl halide

Halogen bonded to a carbon in an aromatic ring

Aryl halide

Ethyl group

Two-carbon substituent branch

All substituents are functional groups, but not all functional groups are substituents

False. Substituents is any group of atoms that replaces a hydrogen on a parent hydrocarbon chain, whereas a functional group is a specific substituent that dictates the characteristic chemical reactions of a molecule.

Meth-

1 carbon

Eth-

2 carbons

Prop-

3 carbons

But-

4 carbons

Pent-

5 carbons

Hex-

6 carbons

Hept-

7 carbons

Oct-

8 carbons

Non-

9 carbons

Dec-

10 carbons

Standard layout of IUPAC nomenclature

Prefix (secondary substituent) + parent carbon chain (bond type) + suffix (primary substituent)

Hierarchy order for IUPAC suffixes

Carboxylic acids > aldehydes > ketones > alcohols > alkenes/alkynes > alkanes/halides

Aldehyde suffix

-al

Ketone suffix

-one

Carboxylic acid suffix

-oic acid

Ester suffix

-oate

Amide suffix

-amide

Halide prefix

halo-

Alcohol prefix

Hydroxy-

Amine prefix

Amino-

Nitro prefix

nitro-

Amide vs amine

Both have nitrogen, but amide has a carbonyl

Phenyl group C₆H_5^—

Cyclic chemical group derived from benzene with one hydrogen atom removed

Benzyl group C₆H₅CH₂—

Benzene ring + methylene

Benzene C₆H₆

Aromatic ring alternating double/single bonds with 6 carbons

Alkyl halide nomenclature

Fluoro-, chloro-, bromo-, iodo-

Alcohol nomenclature

hydroxy-, -ol

Ether nomenclature

alkoxy-, methoxy-

Amine nomenclature

-amine, amino-

Thiol nomenclature

-thiol, mercapto-

Aldehyde nomenclature

-al, oxo-

Ketone nomenclature

-one, oxo-, keto-

Carboxylic acid nomenclature

-oic acid, carboxy-

Ester nomenclature

-oate

Amide nomenclature

-amide, amido-

Acid anhydride nomenclature

-oic anhydride

Isopropyl / propan-2-yl

A branched chain of 3 carbons attached to the main molecule at the middle carbon

Butyl / isobutyl/ sec-butyl / tert-butyl

Various 4-carbon branching motifs

But- vs tetra-

But- indicates a parent carbon chain of four carbons, whereas tetra- is a numerical multiplier indicating four identical substituent groups attached to that carbon

Hydrocarbon suffixes

-ane (single bonds) -ene(C=C) -yne (C≣C)

Hydrocarbon combinations

-diene → 2 double bonds. -triene → 3 double bonds. -diyne → 2 triple bonds

Locant

number or letter that shows position of atom/group/chain on parent

tert-butyl / 1,1-dimethylethyl

four-carbon branched alkyl group

n-

Stands for “normal” and means a molecule has a straight, continuous, unbranched chain of carbon atoms

neo-

All but two carbons form a continuous chain (common)

Disulfide

Covalent bond between two sulfur atoms

Carboxylate

RCOO^-`

Imine

C=N

Nitro

-NO₂