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 14 + 19O 2 → 12CO 2 + 14H 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