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IMPORTANT ORGANIC REACTIONS

Presentation created by S. Schlosz. Information by N. Solomons, K. Dilraj & S. Schlosz. IMPORTANT ORGANIC REACTIONS. What must you be able to do?. identify the types of reactions that hydrocarbons undergo. explain what happens during each type of reaction.

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IMPORTANT ORGANIC REACTIONS

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  1. Presentation created by S. Schlosz Information by N. Solomons, K. Dilraj & S. Schlosz IMPORTANT ORGANIC REACTIONS

  2. What must you be able to do? • identify the types of reactions that hydrocarbons undergo. • explain what happens during each type of reaction. • compare the reactivity of different hydrocarbons.

  3. Conditions: Heat OR sunlight; Reactants: alkane + X2 (Br, Cl, I, F) Process = halogenation; Products = haloalkane + hydrogen halide NOTE: This is a hydrogen halide [acid]. OXIDATION (COMBUSTION) Conditions: Heat and high pressure OR heat and catalyst Process = cracking Products = alkene(s) + alkane(s) Reactions of Alkanes: SUBSTITUTION Alkane becomes haloalkane 2C6H14 + 19O2 → 12CO2 + 14H2O Alkane + oxygen → carbon dioxide + water + energy REACTIONS OF ALKANES ELIMINATION Alkane becomes alkene(s) and alkane(s) with shorter chain

  4. REACTIONS OF ALKENES Process = halogenation Product = haloalkane No water present; Process = hydrohalogenation Product = haloalkane Major product: H atom attaches to the C atom already having the greater number of H atoms / / NOTE: This is Markovnikov’s Rule for ADDITION Reactions. In presence of excess H2O and acid as catalyst Process = hydration; product = alcohol Major product: H atom attaches to the C atom already having the greater number of H atoms Pt, Pd or Ni as catalyst Process = hydrogenation; product = alkane / Pt 150C NOTE: Only minor product shown. This is the CIS structure. The major product will have the TRANS structure [Cl on opposite sides of the different Carbons] ADDITION Alkene becomes alkane, alcohol or haloalkane NOTE: The acid must be dilute H2SO4 or H3PO4. Cannot use HNO3 & HCl as they produce gases.

  5. H Haloalkanesare important compounds that are used as anesthetics (trichloromethane), solvents and dry cleaning agents. Tetrachloroethane Trichloromethane (chloroform) Tetrachloromethane (Carbon tetrachloride) Halo-ethane

  6. Conditions: concentrated strong base (NaOH, KOH, LiOH), heat • Process = dehydrohalogenation; Products = alkene + NaBr + H2O • Major product: The one where the H atom is removed from the C atom with the least number of H atoms (most substituted double bond forms i.e. double bond with most alkyl groups forms) / NOTE: This is VASILY SAYTZEFF’s Rulefor ELIMINATION Reactions. Conditions: Dilute strong base (NaOH, KOH, LiOH), mild heat Substitution - hydrolysis; Products = alcohol + NaBr (KBr or LiBr) Conditions: Add water, mild heat Substitution – hydrolysis; Products = alcohol + HBr HaloAlkanes undergo: ELIMINATION Haloalkane becomes alkene REACTIONS OF HALOALKANES SUBSTITUTION Haloalkane becomes alcohol

  7. H2SO4 / Substitution with hydrogen halide Products = haloalkane + H2O Reactants needed: Primary & secondary alcohols: NaBr + H2SO4 Tertiary alcohols: HBr (or HCl) H H OH H – C – C– C – H H H H H H O H H – C – C – C – H H H H - C - H H • Elimination of H2O – dehydration; Products = alkene + H2O • Major product: The one where the H atom is removed from the C atom with the least number of H atoms (most substituted double bond forms i.e. double bond with most alkyl groups) • To produce gaseous alkenes: pass alcohol over heated AlCl3 H H H – C – C – O – H H H REACTIONS OF ALCOHOLS SUBSTITUTION Alcohol becomes haloalkane ELIMINATION Alcohol becomes alkene REACTIONS OF ALCOHOLS ESTERIFICATION Acid catalysed condensation Alcohol + carboxylic acid → ester + water H2SO4

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