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VICChemistryQuick questions

Unit 4: How are organic compounds categorised, analysed and used?

Quick questions on Organic reactions and reaction pathways: VCE Chemistry Unit 4

14short Q&A pairs drawn directly from our worked dot-point answer. For full context and worked exam questions, read the parent dot-point page.

What is the five reaction types you need?
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1. Substitution (R-X to R-Y). One atom or group on a saturated carbon is replaced by another. The skeleton stays the same.
What is markovnikov's rule?
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For an unsymmetric alkene reacting with an unsymmetric reagent like HBr or H2O, the H goes to the carbon with more hydrogens (the less-substituted end), and the other group (Br, OH) goes to the carbon with fewer hydrogens (the more-substituted end). The major product is the one with the more-substituted carbocation intermediate.
What is multi-step pathway design?
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The classic alkane-to-ester pathway is:
What is 1. Substitution?
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One atom or group on a saturated carbon is replaced by another. The skeleton stays the same.
What is 2. Addition?
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Two atoms or groups add across C=C or C triple C, converting the molecule from unsaturated to (more) saturated.
What is 3. Oxidation?
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Acidified K2Cr2O7 / H2SO4 (or KMnO4 / H2SO4) under reflux.
What is 4. Condensation?
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Two small molecules combine into a larger molecule with loss of a small molecule (usually water). The key example is esterification:
What is 5. Hydrolysis?
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Adding water (often with acid or base catalyst) cleaves an ester or amide bond back to the carboxylic acid + alcohol (or carboxylic acid + amine).
What is forgetting catalyst/conditions?
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A reagent without conditions is not a complete answer. Reflux is the default for liquid-phase reactions; UV light for the alkane chlorination; H2SO4 for esterification.
What is oxidising a tertiary alcohol?
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Tertiary alcohols do not oxidise under K2Cr2O7 / H2SO4 (no H on the OH carbon to lose). A "no reaction" answer is correct.
What is adding HBr to an alkene the wrong way?
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Markovnikov: H goes to the side with more Hs already (less substituted side); Br goes to the more substituted side.
What is forgetting that esterification is reversible?
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State the equilibrium and how to drive it (excess alcohol or acid, removing water).
What is confusing condensation and addition?
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Condensation produces a small molecule by-product (water). Addition does not (everything ends up in the product).
What is using KOH in water for elimination?
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Elimination requires concentrated alkali in ethanol (and heat). KOH in water gives substitution (haloalkane to alcohol).

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