Important Common Names and Substituents – MCAT Content


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Organic chemistry runs two naming systems side by side! IUPAC names follow a strict set of rules. Common names, like acetone and isopropyl alcohol, come from history and everyday use, and the MCAT uses both.

This study note covers the common names and substituents you’ll meet most, with a structure for each one, so you can turn a name into a drawing on test day. Let’s get started!

What Are Substituents in Organic Chemistry?

A substituent is an atom or group that replaces a hydrogen on a molecule’s parent chain or ring. Substituents come first in a name as prefixes, and the parent chain comes last. In 2-methylpentane, methyl is the substituent and pentane is the parent!

Carbon substituents swap the -ane ending for -yl, so methane becomes methyl and ethane becomes ethyl. Chemists also write R for any alkyl group and Ar for any aryl (aromatic ring) group.

The IUPAC naming rules give every molecule one systematic name. Many molecules kept an older common name too, and some of those, like acetone, are what everyone calls them!

Learn both names for the same molecule

A question can say isopropyl alcohol while the answer choices say 2-propanol. They’re the same molecule, and spotting that is a free point 🙂

Organic chemistry makes up about 15% of the Chem/Phys section, by the AAMC’s estimate, and names show up in every orgo passage. This page builds on our MCAT organic chemistry nomenclature guide and its naming fundamentals.

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Alkyl Substituents: Isopropyl, Sec-Butyl, Tert-Butyl and More

With one hydrogen removed, a carbon chain becomes an alkyl group that can bond to something else. Here are the ones you’ll see most, with their common names and their systematic IUPAC names!

Common nameCondensed formulaCarbonsIUPAC substituent name
Methyl−CH31methyl
Ethyl−CH2CH32ethyl
n-Propyl−CH2CH2CH33propyl
Isopropyl−CH(CH3)23propan-2-yl (1-methylethyl)
n-Butyl−CH2CH2CH2CH34butyl
sec-Butyl−CH(CH3)CH2CH34butan-2-yl (1-methylpropyl)
Isobutyl−CH2CH(CH3)242-methylpropyl
tert-Butyl−C(CH3)34tert-butyl (1,1-dimethylethyl)
Neopentyl−CH2C(CH3)352,2-dimethylpropyl

What n-, iso-, sec-, tert- and neo- mean

All four butyl groups have four carbons. The prefix tells you which carbon makes the attachment, and that’s what you need to draw the structure from the name!

Common names and substituents in MCAT organic chemistry nomenclature: n-propyl and n-butyl attach at a primary carbon, isopropyl and sec-butyl at a secondary carbon, isobutyl at a primary CH2 and tert-butyl at a tertiary carbon
  • An n- (normal) group is an unbranched chain, attached at an end carbon.
  • An iso- group’s far end splits into two methyls, (CH3)2CH−, like isopropyl and isobutyl.
  • A sec- (secondary) group attaches through a carbon bonded to two other carbons.
  • A tert- (tertiary) group attaches through a carbon bonded to three other carbons.
  • A neo- group has a carbon carrying three methyls at the far end, so neopentyl is a CH2 attached to a tert-butyl group.
Sec-butyl and isobutyl get swapped a lot

Both have one branch. Check the carbon that bonds to the molecule. In sec-butyl it’s a secondary CH, and in isobutyl it’s a CH2 with the branch one carbon further out!

IUPAC’s 2013 rules prefer the systematic names for isobutyl, sec-butyl and neopentyl, and they keep isopropyl and tert-butyl. You’ll still see all five common names in textbooks and exam questions, so it helps to know both versions!

Vinyl, Allyl, Phenyl and Benzyl Groups

These four carry a double bond or a benzene ring, and they come in two pairs. In each pair, the second group is the first one with a CH2 added between it and the rest of the molecule!

Vinyl CH2=CH- and phenyl C6H5- bond straight to the molecule, while allyl CH2=CHCH2- and benzyl C6H5CH2- have one CH2 in between
  • Vinyl (CH2=CH−, IUPAC ethenyl) bonds through a carbon of the double bond. Vinyl chloride is the building block of PVC plastic.
  • Allyl (CH2=CHCH2−) bonds through the CH2 next to the double bond. The name comes from garlic, Allium sativum.
  • Phenyl (C6H5−, written Ph) is a benzene ring bonded straight to the molecule. It’s the simplest aryl group.
  • Benzyl (C6H5CH2−, written Bn) is a benzene ring with a CH2 between it and the molecule.
Phenyl or benzyl? Count to the ring

If the ring carbon bonds to the molecule, it’s phenyl. If a CH2 sits between them, it’s benzyl. Benzene itself is C6H6, so phenyl has 5 hydrogens on the ring and benzyl keeps those 5 and adds 2 more!

List of Substituents in Organic Chemistry

Beyond the carbon groups, these are the substituents you’ll run into most often! Each has a prefix name for when it isn’t the molecule’s main functional group.

SubstituentFormulaPrefix nameWhat to remember
Fluorine−Ffluoro-The C−F bond is one of the strongest single bonds in organic chemistry
Chlorine−Clchloro-Found in solvents like chloroform and in many pesticides
Bromine−Brbromo-Bromide is a good leaving group in substitution and elimination
Iodine−Iiodo-Iodide is the best leaving group of the halides (I− > Br− > Cl− > F−)
Hydroxyl−OHhydroxy-Alcohols and phenols, and it hydrogen bonds
Amino−NH2amino-Amines and amino acids, and it’s basic
Nitro−NO2nitro-Strongly electron-withdrawing
Cyano−C≡Ncyano-The group in nitriles
Alkoxy−OR, like −OCH3methoxy-, ethoxy-The prefix form of an ether
Carbonyl oxygen=Ooxo-A ketone or aldehyde oxygen named as a prefix
Aldehyde−CHOformyl-Sits at the end of a chain
Carboxyl−COOHcarboxy-The acid group named as a prefix
AcetylCH3CO−acetyl-The acyl group from acetic acid

Which groups get a prefix depends on priority. The highest-priority group takes the suffix and every other group becomes a prefix. Our priority ordering of functional groups notes walk through the full ranking!

Prefix or suffix? Alanine shows you

Alanine’s IUPAC name is 2-aminopropanoic acid. The carboxylic acid outranks the amine, so the acid takes the suffix (-oic acid) and the amine becomes the prefix amino-.

Ethers have two kinds of names. In IUPAC names they take an alkoxy prefix, like methoxymethane. Their common names list both alkyl groups and add ether, like dimethyl ether and diethyl ether.

Common Names of Organic Compounds

Some molecules go by their common names almost everywhere! These tables pair each one with its IUPAC name and formula. The carbonyl compounds, with their own naming pattern, are in the next section.

Hydrocarbons and alcohols

Common nameIUPAC nameFormulaWhere you’ll see it
EthyleneetheneCH2=CH2The monomer of polyethylene
PropylenepropeneCH2=CHCH3The monomer of polypropylene
AcetyleneethyneHC≡CHWelding torches
Methyl alcohol (wood alcohol)methanolCH3OHSolvent and antifreeze
Ethyl alcoholethanolCH3CH2OHThe alcohol in drinks
Isopropyl alcoholpropan-2-ol (2-propanol)(CH3)2CHOHRubbing alcohol
tert-Butyl alcohol2-methylpropan-2-ol(CH3)3COHA tertiary alcohol
Ethylene glycolethane-1,2-diolHOCH2CH2OHAntifreeze
The alcohol pattern

A common alcohol name is the alkyl group plus the word alcohol. Ethyl alcohol is ethanol, isopropyl alcohol is propan-2-ol, and tert-butyl alcohol is 2-methylpropan-2-ol. Our alcohol and ether naming notes have more examples!

Aromatic compounds

Benzene with one substituent often keeps an older name. IUPAC still uses several of them, like phenol, aniline and benzoic acid, as official names!

Common nameIUPAC nameFormulaSubstituent on the ring
ToluenemethylbenzeneC6H5CH3Methyl
PhenolphenolC6H5OHHydroxyl
Anilineaniline (benzenamine)C6H5NH2Amino
AnisolemethoxybenzeneC6H5OCH3Methoxy
BenzaldehydebenzaldehydeC6H5CHOAldehyde (it smells like almonds)
Benzoic acidbenzoic acidC6H5COOHCarboxyl (a food preservative)

Ethers, esters and halides

Common nameIUPAC nameFormulaWhere you’ll see it
Diethyl etherethoxyethaneCH3CH2OCH2CH3Lab solvent
Ethyl acetateethyl ethanoateCH3COOCH2CH3Lab solvent
Acetic anhydrideethanoic anhydride(CH3CO)2OAcetylating reagent
ChloroformtrichloromethaneCHCl3Solvent
Methylene chloridedichloromethaneCH2Cl2Extraction solvent, denser than water

Form-, Acet- and Propion-: Common Names for Carbonyls

Aldehydes and carboxylic acids share one set of common-name prefixes, and each prefix is a carbon count. Learn four prefixes and you’ve got eight names!

Common names of organic compounds: form- means 1 carbon (formaldehyde, formic acid), acet- means 2 (acetaldehyde, acetic acid) and propion- means 3 (propionaldehyde, propionic acid), while acetone has 3
Prefix = carbon count

form- is 1 carbon, acet- is 2, propion- is 3 and butyr- is 4. Butyraldehyde is butanal, and butyric acid (the smell of rancid butter) is butanoic acid!

Ketones

For ketones, the common name lists the two alkyl groups on the carbonyl in alphabetical order and adds ketone. Butanone is ethyl methyl ketone, which you’ll also see written as methyl ethyl ketone (MEK).

Acetone (propanone) is the simplest ketone and the solvent in many nail polish removers. Its three carbons make it the exception to the acet- pattern!

Where three of these names come from

  • Formaldehyde (methanal), the simplest aldehyde, is used in embalming and disinfection.
  • Formic acid (methanoic acid) is in ant stings. The name comes from formica, Latin for ant.
  • Acetic acid (ethanoic acid) is the acid in vinegar, and acetaldehyde (ethanal) oxidizes to it.

Our aldehyde and ketone naming notes and carboxylic acid naming notes go deeper on each family!

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How Substituents Change Reactions on the MCAT

Because a name tells you the structure, it also tells you a lot about the reaction. Here’s what the common substituent names tell you before you draw anything!

The name tells youSo expect
A methyl or primary alkyl halide (like n-butyl bromide)SN2, since the carbon is open to backside attack
A tertiary alkyl halide (like tert-butyl bromide)SN1 or E1, or E2 with a strong base. Never SN2, since the carbon is too crowded
Tert-butyl, isopropyl and other branched groupsMore stable carbocations. Alkyl groups donate electron density, so tertiary > secondary > primary
An allyl or benzyl group next to a carbocationExtra stability from resonance
A primary alcohol (like ethyl alcohol)Oxidizes to an aldehyde, then on to a carboxylic acid
A secondary alcohol (like isopropyl alcohol)Oxidizes to a ketone (acetone)
A tertiary alcohol (like tert-butyl alcohol)Resists oxidation
An aldehyde or a ketoneNucleophilic addition, faster for the aldehyde

Aldehydes react faster than ketones in nucleophilic addition. A ketone’s second alkyl group crowds the carbonyl carbon and donates electron density, which makes that carbon less positive.

Our SN1 vs SN2 notes and alcohol redox notes cover both reactions in full!

Substituents on a benzene ring

On a benzene ring, a substituent changes how fast the ring reacts with electrophiles and where the next group lands. That splits ring substituents into three groups.

  • Electron-donating groups (like −OH, −NH2, −OCH3 and alkyl groups) activate the ring and direct ortho and para.
  • Electron-withdrawing groups (like −NO2, −COOH and −CHO) deactivate the ring and direct meta.
  • Halogens deactivate the ring but still direct ortho and para.
Rank tert-butyl, isopropyl and n-propyl bromide for SN1

SN1 runs through a carbocation, so the most stable carbocation wins. Tert-butyl bromide forms a tertiary carbocation, isopropyl bromide a secondary one and n-propyl bromide a primary one.

So the order is tert-butyl > isopropyl > n-propyl. Nice work if the names did the work for you!

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Substituents You’ll See in Amino Acids

The substituent names come back in biochemistry! Several amino acid side chains are groups from this page, so the names help you picture the structures.

Amino acidSide chainSubstituent name
Alanine−CH3Methyl
Valine−CH(CH3)2Isopropyl
Leucine−CH2CH(CH3)2Isobutyl
Isoleucine−CH(CH3)CH2CH3sec-Butyl
Phenylalanine−CH2C6H5Benzyl
Tyrosine−CH2C6H4OH4-Hydroxybenzyl
Serine−CH2OHHydroxymethyl
Leucine and isoleucine

Leucine and isoleucine are isomers with the same formula, and their side chains are isobutyl and sec-butyl. If you can tell those two groups apart, you can tell these two amino acids apart!

Along with its side chain, every amino acid carries an amino group and a carboxyl group. Our amino acid structure notes walk through all 20 side chains!

Common Names and Substituents: Terms to Know

Here’s a quick review of the terms on this page!

TermMeaning
SubstituentAn atom or group that replaces a hydrogen on the parent chain or ring
Common nameA name from history or everyday use, like acetone or isopropyl alcohol
IUPAC nameThe systematic name built from IUPAC’s rules, like propanone or propan-2-ol
Alkyl group (R)A carbon chain minus one hydrogen, named with -yl
Aryl group (Ar)An aromatic ring as a substituent. Phenyl is the simplest
Primary, secondary, tertiary carbonA carbon bonded to one, two or three other carbons
Vinyl and allylCH2=CH− and CH2=CHCH2−
Phenyl and benzylC6H5− and C6H5CH2−
Halo groupsFluoro, chloro, bromo and iodo
Carbonyl groupC=O, found in aldehydes, ketones, carboxylic acids and their derivatives

Practice Questions

Try these before you open the answers!

Question 1

What is the IUPAC name for CH3OH?

A) Ethanol
B) Methanol
C) Propanol
D) Isopropanol

Show the answer

B. Methanol is the IUPAC name. Its common names are methyl alcohol and wood alcohol, and it’s used as a solvent and antifreeze.

Question 2

Which substituent is represented by the group −NH2?

A) Hydroxyl
B) Methyl
C) Amino
D) Carbonyl

Show the answer

C. The −NH2 group is an amino group, found in amines and amino acids.

Question 3

Which alkyl group bonds to the rest of the molecule through a tertiary carbon?

A) Isobutyl
B) sec-Butyl
C) tert-Butyl
D) n-Butyl

Show the answer

C. Tert-butyl attaches through a carbon bonded to three methyl groups. Sec-butyl attaches through a secondary carbon, and isobutyl and n-butyl through a primary CH2.

Question 4

A molecule carries a −CH2CH=CH2 group. What is it called?

A) Vinyl
B) Allyl
C) Propyl
D) Benzyl

Show the answer

B. Allyl is a CH2 attached to a vinyl group. Vinyl has no CH2 spacer, propyl has no double bond and benzyl carries a benzene ring.

Question 5

What is the common name of propanone?

A) Acetaldehyde
B) Propionaldehyde
C) Acetone
D) Acetic acid

Show the answer

C. Propanone is acetone, the simplest ketone. Acetaldehyde is ethanal, propionaldehyde is propanal and acetic acid is ethanoic acid.

Common Names and Substituents FAQs

What are substituents in organic chemistry?

Substituents are atoms or groups that replace a hydrogen on a molecule’s parent chain or ring, like methyl, chloro or hydroxy. They’re named as prefixes in front of the parent name!

What’s the difference between a common name and an IUPAC name?

An IUPAC name comes from a fixed set of rules, so it describes the structure. A common name comes from history or everyday use. Acetone and propanone are the same molecule.

What is the common name of CH3OH?

Methyl alcohol, also called wood alcohol. Its IUPAC name is methanol.

What’s the difference between phenyl and benzyl?

Phenyl (C6H5−) is a benzene ring bonded straight to the molecule. Benzyl (C6H5CH2−) has a CH2 between the ring and the molecule.

What’s the difference between acetone and formaldehyde?

Acetone, (CH3)2CO, is a three-carbon ketone called propanone. Formaldehyde, HCHO, is a one-carbon aldehyde called methanal. Both have a carbonyl group!

Do you need to know common names for the MCAT?

Yes. Questions can use names like acetone, acetic acid, isopropyl alcohol or tert-butyl without giving the IUPAC name. The tables on this page and our MCAT organic chemistry nomenclature guide cover the ones to know!

Final Thoughts on Common Names and Substituents

Common names and substituents are the vocabulary of organic chemistry. Once the prefixes click, a name like tert-butyl alcohol turns into a structure in your head, and orgo passages get faster to read!

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Supplemental Resources

Want to go deeper on this topic? Here's where to read, watch and practice it next.

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  • Kaplan MCAT Organic Chemistry Review 2026-2027, §1.1 and §1.3 and §1.4

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