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

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Presentation on theme: "IMPORTANT ORGANIC REACTIONS Presentation created by S. Schlosz Information by N. Solomons, K. Dilraj & S. Schlosz."— Presentation transcript:

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

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 Reactions of Alkanes: OXIDATION (COMBUSTION) 2C 6 H O 2 → 12CO H 2 O Alkane + oxygen → carbon dioxide + water + energy Conditions: Heat OR sunlight; Reactants: alkane + X 2 (Br, Cl, I, F) Process = halogenation; Products = haloalkane + hydrogen halide Conditions: Heat and high pressure OR heat and catalyst Process = crackingProducts = alkene(s) + alkane(s) ELIMINATION Alkane becomes alkene(s) and alkane(s) with shorter chain SUBSTITUTION Alkane becomes haloalkane REACTIONS OF ALKANES NOTE: This is a hydrogen halide [acid]. HALOGEN (as found in the periodic table) Normally diatomic HALIDE (the state of the Halogen after it has received an electron via bonding) F (F 2 ) FluorineF - (Fluoride) Cl (Cl 2 ) ChlorineCl - (Chloride) Br (Br 2 ) BromineBr - (Bromide) I (I 2 ) IodineI - (Iodide)

4 REACTIONS OF ALKENES Process = halogenation Product = haloalkane Pt, Pd or Ni as catalyst Process = hydrogenation; product = alkane ADDITION Alkene becomes alkane, alcohol or haloalkane NOTE: minor productCIS major productTRANS 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]Pt 150  C 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: Markovnikov’s Rule This is Markovnikov’s Rule for ADDITION Reactions. In presence of excess H 2 O 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 / NOTE: aciddilute The acid must be dilute H 2 SO 4 or H 3 PO 4. Cannot use HNO 3 & HCl as they produce gases.

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

6 HaloAlkanes undergo: SUBSTITUTION Haloalkane becomes alcohol REACTIONS OF HALOALKANES ELIMINATION Haloalkane becomes alkene  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: VASILY SAYTZEFF’s Rule This is VASILY SAYTZEFF’s Rule for ELIMINATION Reactions. Conditions: Add water, mild heat Substitution – hydrolysis; Products = alcohol + HBr Conditions: Dilute strong base (NaOH, KOH, LiOH), mild heat Substitution - hydrolysis; Products = alcohol + NaBr (KBr or LiBr)

7 Elimination of H 2 O – dehydration; Products = alkene + H 2 O  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 AlCl 3 H 2 SO 4 / REACTIONS OF ALCOHOLS REACTIONS OF ALCOHOLS SUBSTITUTION Alcohol becomes haloalkane ELIMINATION Alcohol becomes alkene Substitution with hydrogen halide Products = haloalkane + H 2 O Reactants needed: Primary & secondary alcohols: NaBr + H 2 SO 4 Tertiary alcohols: HBr (or HCl) ESTERIFICATION Acid catalysed condensation Alcohol + carboxylic acid → ester + water H 2 SO 4 Primary Alcohols O-H 1 other Carbon The O-H group is attached to a Carbon which is attached to 1 other Carbon Secondary Alcohols O-H 2 other Carbons The O-H group is attached to a Carbon which is attached to 2 other Carbons Tertiary Alcohols O-H 3 other Carbons The O-H group is attached to a Carbon which is attached to 3 other Carbons H H COH H – C – C – O – H H H H O H C H – C – C – C – H H H H H H O H H – C – C – C – H H H H - C - H H


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