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Logical Halogenoalkane Reactions

Halogenoalkanes react with sodium hydroxide (NaOH) through substitution and elimination reactions. In substitution, the halogen is replaced by an OH group, while in elimination, an alkene is formed. The type of reaction depends on the structure of the halogenoalkane, with primary halogenoalkanes favoring substitution and tertiary ones favoring elimination.

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9 views2 pages

Logical Halogenoalkane Reactions

Halogenoalkanes react with sodium hydroxide (NaOH) through substitution and elimination reactions. In substitution, the halogen is replaced by an OH group, while in elimination, an alkene is formed. The type of reaction depends on the structure of the halogenoalkane, with primary halogenoalkanes favoring substitution and tertiary ones favoring elimination.

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Halogenoalkane Reactions with NaOH

1. Substitution Reactions with Sodium Hydroxide (NaOH)


When halogenoalkanes react with aqueous sodium hydroxide in a 50:50 mixture of
ethanol and water under reflux, a nucleophilic substitution reaction occurs, where the
halogen is replaced by an OH group.

(a)(i) What is “heated under reflux” and why is it used?


Reflux involves heating a reaction mixture in a container with a condenser placed
vertically on top. This setup prevents the loss of volatile substances by condensing
vapors and returning them to the flask. It ensures the reaction proceeds for a long time
at boiling temperature without losing reactants.

(a)(ii) Reaction of 1-bromopropane with NaOH


Equation:
CH₃CH₂CH₂Br + OH⁻ → CH₃CH₂CH₂OH + Br⁻

This is a nucleophilic substitution reaction. The product is propan-1-ol.

(b) Products of similar substitution reactions:


(i) 2-bromopropane + NaOH → propan-2-ol

(ii) 1-bromobutane + NaOH → butan-1-ol

2. Elimination Reactions with Sodium Hydroxide (NaOH)


When halogenoalkanes react with hot concentrated sodium hydroxide in ethanol
(anhydrous conditions), an elimination reaction can occur, forming an alkene.

(a) 2-bromopropane undergoes elimination


Equation:
CH₃CHBrCH₃ + OH⁻ → CH₂=CHCH₃ + H₂O + Br⁻

This reaction gives propene.

(b) 2-bromobutane reactions


(i) Substitution → CH₃CH(OH)CH₂CH₃ (butan-2-ol)

(ii) Elimination → Mixture of:

- But-1-ene: CH₂=CHCH₂CH₃

- But-2-ene: CH₃CH=CHCH₃ (cis/trans isomers)


3. Substitution vs Elimination: What dominates?
Whether a halogenoalkane undergoes mainly substitution or elimination with NaOH
depends on the structure of the halogenoalkane:

(i) Primary halogenoalkane → Mainly substitution

(ii) Secondary halogenoalkane → A mixture of substitution and elimination

(iii) Tertiary halogenoalkane → Mainly elimination

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