Types of Organic Reactions

The Core of Organic Chemistry

Abstract glowing molecular bonds

What's in this lesson: You will learn to identify and classify the four fundamental types of organic reactions: Substitution, Addition, Elimination, and Rearrangement.

Why this matters: Every biological process in your body and every synthetic material you use is the result of organic reactions. Recognizing these patterns allows you to predict how molecules will behave and transform.

In organic chemistry, billions of known reactions can be boiled down to just a few simple patterns. It is all about the breaking and making of bonds.

The 4 Reaction Archetypes

Organic molecules undergo structural changes through four primary mechanisms. Click each card to reveal its core definition.

1. Substitution
One atom or group replaces another. (A swap)
2. Addition
Two molecules combine into one product. (A merger)
3. Elimination
One molecule splits into two fragments. (A break-up)
4. Rearrangement
Atoms shuffle within a molecule to form an isomer.

Take a mental note of these four actions: Swap, Merge, Split, Shuffle.

Type 1: Substitution Reactions

Substitution diagram

Definition: A reaction in which an attacking species (nucleophile, electrophile, or free radical) replaces another atom or group in the substrate.

In organic chemistry, this is typically represented as a substrate (R-X) reacting with an attacking group (Y).

Interactive: Click anywhere in this box to perform the substitution!

R
X
+
Y

Success! The attacking group (Y) has replaced the leaving group (X).

Substitution in Action

Let's look at a real chemical example of a substitution reaction.

CH₃–CH₂–Cl + KOH(aq)CH₃–CH₂–OH + KCl

Reactants: Chloroethane + aqueous Potassium Hydroxide.

Products: Ethanol + Potassium Chloride.

Knowledge Check

In the reaction CH₃–Br + NaOH(aq) → CH₃–OH + NaBr, what describes the structural change?

Two smaller molecules merged into one large one.
The -OH group replaced the -Br atom on the carbon chain.
A double bond was formed by removing atoms.
The atoms shuffled around without any other reactant.

Type 2: Addition Reactions

Addition diagram

Definition: When two molecules combine to form only one product molecule.

This process typically requires the reactant to have a double or triple bond (pi bond). The pi bond breaks, allowing new atoms to attach to the carbon skeleton.

Interactive: Click to break the double bond and add molecules!

C=C + X-Y

Addition in Action

Here is how an alkene reacts with a hydrogen halide.

CH₂ = CH₂ + HCl → CH₃–CH₂–Cl

Reactants

Ethene: Contains a carbon-carbon double bond.

HCl: Hydrogen chloride molecule.

Product

Chloroethane: The double bond is gone. H attached to one carbon, Cl to the other.

Notice how two distinct reactant molecules merged into a single product molecule. This is the hallmark of an addition reaction.

Knowledge Check

Which of the following visual cues is the strongest indicator of an addition reaction?

Two reactants forming exactly one product molecule.
One reactant splitting into multiple products.
Two reactants forming two new products.
A single reactant changing its internal structure.

Type 3: Elimination Reactions

Elimination diagram

Definition: When one molecule splits into two fragment molecules.

Elimination is the exact opposite of addition. Compounds containing a C–C single bond are converted into compounds containing a C=C double bond by removing atoms or groups from adjacent carbon atoms.

Interactive: Click to remove atoms and form a double bond!

X-C-C-Y

Elimination in Action

Let's look at the elimination of chloroethane. Note the specific reagent condition required.

CH₃–CH₂–Cl + KOH(alc), Δ → CH₂ = CH₂ + KCl + H₂O
Crucial Detail: KOH(aq) causes Substitution, but KOH(alc) (alcoholic) with heat (Δ) causes Elimination!

In this reaction, H and Cl are eliminated from adjacent carbon atoms to form the double bond in Ethene.

Knowledge Check

You have a sample of Chloroethane and you want to produce Ethene (a molecule with a double bond). Which reagent should you use?

Aqueous KOH — because it favors substitution.
Alcoholic KOH with heat — because it favors elimination.
HCl gas — because it favors addition.
Water with heat — because it favors rearrangement.

Type 4: Rearrangement Reactions

Rearrangement diagram

Definition: A reaction in which either the carbon skeleton, the functional group, or both are modified to form an isomer.

Nothing is added, and nothing is completely lost. The atoms simply "shuffle" into a new, often more stable, configuration.

Interactive: Click to shuffle the atoms!

A-B-C

Rearrangement in Action

A classic example is tautomerism, where a proton (H⁺) shifts its position within the molecule.

CH₂ = CH–OH → CH₃–CHO

Ethenol (Vinyl Alcohol)

Formula: C₂H₄O

Has a double bond (C=C) and an alcohol group (-OH).

Ethanal (Acetaldehyde)

Formula: C₂H₄O

The double bond moved to the oxygen (C=O), and the H moved to the carbon. It is an aldehyde.

Notice the molecular formula (C₂H₄O) remained exactly the same! Only the connectivity changed.

Knowledge Check

Which feature distinguishes a rearrangement reaction from the other three types?

The reactant and product have the same exact molecular formula (they are isomers).
Two reactant molecules are required.
A smaller molecule like water is lost.
An external attacking nucleophile is always needed.

Summary of Reaction Types

Review the four types before moving on to the final assessment.

Type Core Action Key Identifier
Substitution Swap A + BC → AC + B
Addition Combine A + B → C (double bond breaks)
Elimination Split C → A + B (double bond forms)
Rearrangement Shuffle A → B (A and B are isomers)

Ready for the Assessment?

You will face 5 questions. You need 80% to pass.

Final Assessment

Test your knowledge on the types of organic chemistry reactions.

There are 5 questions. Select the best answer for each.

Question 1

Identify the type of reaction:
CH₃–Br + KOH(aq), Δ → CH₃–OH + KBr

Addition reaction
Elimination reaction
Substitution reaction
Rearrangement reaction

Question 2

Identify the type of reaction:
CH₃–CH = CH₂ + Cl₂ → CH₃–CHCl–CH₂Cl

Addition reaction
Elimination reaction
Substitution reaction
Rearrangement reaction

Question 3

Identify the type of reaction:
CH₃–C=N–OH → CH₃–CONH–C₆H₅ (with H₂SO₄)

Addition reaction
Elimination reaction
Substitution reaction
Rearrangement reaction

Question 4

Identify the type of reaction:
CH₃–CH₂–OH → CH₂=CH₂ + H₂O (conc. H₂SO₄)

Addition reaction
Elimination reaction
Substitution reaction
Rearrangement reaction

Question 5

Which reaction type typically converts a single bond to a double bond by removing atoms?

Addition
Elimination
Substitution
Rearrangement

Your score will appear here after you complete the assessment.