Lesson 6: Haloalkanes: Substitution & Elimination Reactions

NCEA Level 2 Chemistry. Students classify 1°, 2°, 3° haloalkanes, compare KOH(aq) substitution vs KOH(alc) elimination, Saytzeff's Rule, writing Portfolio Section 6.

Lesson at a Glance | He Tirohanga Whakamua

Do NowClassify 1-chloropropane, 2-chloropropane, 2-chloro-2-methylpropane10 min
Reagent DistinctionKOH(aq) substitution vs KOH(alc) elimination15 min
Saytzeff's Rule"The poor get poorer" Major alkene product15 min
Portfolio EntryWrite Section 6: Haloalkanes Substitution vs Elimination10 min
Exit DrillPredict major product for 2-chlorobutane +KOH(alc)5 min

Ngā Whāinga Ako | Learning Intentions

Students will know

  • How to classify haloalkanes as Primary (1), Secondary (2), or Tertiary (3) based on carbon attachments.
  • How solvent conditions switch reaction pathways:
    KOH(aq) aqueous Substitution forming an Alcohol.
    KOH(alc) alcoholic Elimination forming an Alkene.
    NH3(alc) alcoholic Substitution forming an Amine.
  • Saytzeff's Rule: In elimination reactions, Hydrogen is preferentially removed from the adjacent carbon atom with FEWER hydrogens attached ("the poor get poorer"), forming the Major Alkene Product.

Students will demonstrate

  • By predicting major and minor alkene products for 2-chlorobutane elimination.
  • By completing Section 6 of their Level 2 Organic Chemistry Mastery Portfolio.

Curriculum alignment

  • NZC (2007) · Science · Level 7 · Material World: “Investigate and measure the chemical and physical properties of a range of groups of substances, for example, acids and bases, oxidants and reductants, and selected organic and inorganic compounds.”

Do Now | Tīmatanga Whakaaro (10 min)

Solvent Switch Prompt:

"If you react 1-chloropropane with KOH dissolved in water, you get propan-1-ol. What happens if you dissolve the exact same KOH in ethanol solvent instead of water?"

Unpack: Alcoholic solvent (KOH(alc)) acts as a strong base, favouring Elimination of HCl to form propene (C=C). Aqueous solvent (KOH(aq)) acts as a nucleophile, favouring Substitution of Cl for OH to form propan-1-ol!

Saytzeff's Elimination Rule (15 min)

Reaction: 2-chlorobutane (CH3CH(Cl)CH2CH3) + KOH(alc)

🌟 Major Product (~80%): But-2-ene

CH3CH=CHCH3
Hydrogen is removed from C3 (which has 2 H's instead of C1 which has 3 H's). "The poor get poorer!"

⚠️ Minor Product (~20%): But-1-ene

CH2=CHCH2CH3
Hydrogen is removed from C1. Forms a less substituted, less thermodynamically stable double bond.

Reagent Distinction: the Solvent Decides (15 min)

Where this usually goes wrong: students see "KOH" and stop reading. The same reagent gives two entirely different products depending on the solvent and temperature, and exam questions specify it deliberately.

KOH(aq), warm: substitution

In water, hydroxide behaves as a nucleophile and replaces the halogen. The product is an alcohol. Written KOH(aq) or "aqueous potassium hydroxide" — the state symbol is doing real work here.

KOH in ethanol, hot: elimination

In alcoholic solution, hydroxide behaves as a base and removes a hydrogen from the neighbouring carbon. A C=C forms and the product is an alkene. Written KOH(alc) or "ethanolic". Where two alkenes are possible, Saytzeff's rule predicts the major one.

Do this now: predict BOTH products for 2-bromobutane, one for each set of conditions. Then underline the single word in each set that told you which pathway to use.

📁 Organic Chemistry Portfolio — Section 6: Haloalkane Reactions & Saytzeff

Students open their Level 2 Chemistry Portfolio and complete Section 6:

Section 6 Requirements:

1. Classification & Reaction Matrix: Classify 3 haloalkanes (1,2,3) and map reactions with KOH(aq), KOH(alc), and NH3(alc).

2. Saytzeff Application: Draw Major and Minor alkene products for elimination of 2-bromo-2-methylbutane +KOH(alc).

3. Excellence Reagent Rationale: 1-paragraph explanation of why aqueous conditions produce substitution while alcoholic conditions produce elimination.

Exit Verification | Ka Mutu Hoki (5 min)

Exit Check:

"My Section 6 correctly identifies but-2-ene as the major elimination product of 2-chlorobutane using Saytzeff's Rule."

Teacher Planning & NCEA Alignment

NCEA Level 2 Chemistry Alignment (4 Credits External):

  • Haloalkane Reactions: Predict reagents, conditions, and structural formulas for substitution and elimination reactions.
  • Saytzeff's Rule: Justify major and minor alkene products in elimination reactions.

Vocabulary: Primary (1), secondary (2), tertiary (3) haloalkane, substitution, elimination, aqueous KOH, alcoholic KOH, alcoholic NH3, Saytzeff's Rule, major product, minor product.

Other teaching approach: Guided Viewing & Practical Chemistry →