III. SUBSTITUTION REACTIONS 1. 1.1 What is a substitution reaction? $$ \qquad $$ $$ \qquad $$ $$ \qquad $$ $$ \qquad $$ 1.2 Name the homologous series of which the compounds can undergo substitution. $$ \qquad $$ 2. Name the type of substitution reaction that occurs with each of the following inorganic molecules as one of the reactants: 2.1 HCl : $$ \qquad $$ $$ 2.2 \mathrm{Br}_{2} $$ : $$ \qquad $$ 2.3 NaOH : $$ \qquad $$ $$ 2.4 \mathrm{H}_{2} \mathrm{O} $$ : $$ \qquad $$ 3. Ethane reacts with chlorine to prepare chloroethane. 3.1 Write an equation in words for this reaction. $$ \qquad $$ 3.2 Write down the structural formulae for this reaction. 3.3 Name ONE reaction condition required for the reaction in Question 3.1 to occur. $$ \qquad $$ 4. 4.1 Write down the balanced equation for the reaction of 2-methylpropan-2-ol with HBr by the use of structural formulas. Name the products that are formed. 4.2 Is 2-methylpropan-2-ol a primary, secondary or tertiary alcohol? Explain. $$ \qquad $$ $$ \qquad $$ 4.3 State the reaction conditions required for the reaction of the type of alcohol in question 4.2 with HBr . $$ \qquad $$ 5. 5.2 Write the balanced equation for the reaction of propan- 2 -ol with HBr by using structural formulas. Name the products formed. 128 TOPIC 1

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### 1.1 What is a substitution reaction?
A substitution reaction is a type of chemical reaction where one functional group in a chemical compound is replaced by another functional group. In organic chemistry, this often involves the replacement of a hydrogen atom in a hydrocarbon with a different atom or group of atoms.

### 1.2 Name the homologous series of which the compounds can undergo substitution.
The homologous series that can undergo substitution reactions are alkanes and aromatic compounds. Alkanes can undergo substitution reactions with halogens, while aromatic compounds can undergo electrophilic substitution.

### 2. Name the type of substitution reaction that occurs with each of the following inorganic molecules as one of the reactants:
2.1 HCl: **Nucleophilic substitution**  
2.2 $$\mathrm{Br}_{2}$$: **Electrophilic substitution**  
2.3 NaOH: **Nucleophilic substitution**  
2.4 $$\mathrm{H}_{2}\mathrm{O}$$: **Nucleophilic substitution**

### 3. Ethane reacts with chlorine to prepare chloroethane.
3.1 Write an equation in words for this reaction.
Ethane reacts with chlorine in the presence of ultraviolet light to produce chloroethane and hydrogen chloride.

3.2 Write down the structural formulae for this reaction.
The structural formula for the reaction is:
$$
\text{C}_2\text{H}_6 + \text{Cl}_2 \xrightarrow{h\nu} \text{C}_2\text{H}_5\text{Cl} + \text{HCl}
$$

3.3 Name ONE reaction condition required for the reaction in Question 3.1 to occur.
One reaction condition required is the presence of ultraviolet (UV) light.

### 4. 4.1 Write down the balanced equation for the reaction of 2-methylpropan-2-ol with HBr by the use of structural formulas. Name the products that are formed.
The balanced equation is:
$$
\text{(CH}_3\text{)}_3\text{COH} + \text{HBr} \rightarrow \text{(CH}_3\text{)}_3\text{CBr} + \text{H}_2\text{O}
$$
The products formed are bromo-2-methylpropane and water.

4.2 Is 2-methylpropan-2-ol a primary, secondary or tertiary alcohol? Explain.
2-methylpropan-2-ol is a **tertiary alcohol** because the carbon atom that is bonded to the hydroxyl group (–OH) is attached to three other carbon atoms.

4.3 State the reaction conditions required for the reaction of the type of alcohol in question 4.2 with HBr.
The reaction conditions required are typically heating and the presence of an acid catalyst.

### 5. 5.2 Write the balanced equation for the reaction of propan-2-ol with HBr by using structural formulas. Name the products formed.
The balanced equation is:
$$
\text{CH}_3\text{CHOHCH}_3 + \text{HBr} \rightarrow \text{CH}_3\text{CBrCH}_3 + \text{H}_2\text{O}
$$
The products formed are bromo-propan-2-ol and water.
**Substitution Reactions** 1. **Definition:** - A substitution reaction is a chemical process where one functional group in a compound is replaced by another functional group. In organic chemistry, this often involves replacing a hydrogen atom in a hydrocarbon with a different atom or group. 2. **Homologous Series:** - **Alkanes** and **Aromatic Compounds** can undergo substitution reactions. Alkanes react with halogens, while aromatic compounds undergo electrophilic substitution. 3. **Types of Substitution Reactions:** - **2.1 HCl:** Nucleophilic substitution - **2.2 Br₂:** Electrophilic substitution - **2.3 NaOH:** Nucleophilic substitution - **2.4 H₂O:** Nucleophilic substitution 4. **Ethane and Chlorine Reaction:** - **Reaction Equation:** Ethane reacts with chlorine in the presence of ultraviolet light to produce chloroethane and hydrogen chloride. - **Structural Formula:** $$ \text{C}_2\text{H}_6 + \text{Cl}_2 \xrightarrow{h\nu} \text{C}_2\text{H}_5\text{Cl} + \text{HCl} $$ - **Reaction Condition:** Ultraviolet (UV) light 5. **2-Methylpropan-2-ol with HBr:** - **Reaction Equation:** $$ \text{(CH}_3\text{)}_3\text{COH} + \text{HBr} \rightarrow \text{(CH}_3\text{)}_3\text{CBr} + \text{H}_2\text{O} $$ - **Products:** Bromo-2-methylpropane and water - **Alcohol Type:** Tertiary alcohol (attached to three other carbon atoms) - **Reaction Conditions:** Heating and acid catalyst 6. **Propan-2-ol with HBr:** - **Reaction Equation:** $$ \text{CH}_3\text{CHOHCH}_3 + \text{HBr} \rightarrow \text{CH}_3\text{CBrCH}_3 + \text{H}_2\text{O} $$ - **Products:** Bromo-propan-2-ol and water

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