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Organic Reactions

Organic Reactions. PATHWAYS. Example. P roduce propyl ethanoate from propene and ethene : CH 3 -CH=CH 2 + H 2 O  CH 3 -CH 2 -CH 2 OH ( addition reaction) Propene water propan-1-ol CH 2 =CH 2 + H 2 O  CH 3 -CH 2 OH (addition reaction)

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Organic Reactions

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  1. Organic Reactions PATHWAYS

  2. Example • Produce propyl ethanoate from propene and ethene: • CH3-CH=CH2 + H2O CH3-CH2-CH2OH(addition reaction) Propene water propan-1-ol • CH2=CH2+ H2O  CH3-CH2OH (addition reaction) Ethene water ethanol • CH3-CH2OH+ [O]  CH3-CHO + [O] CH3-COOH (oxidation of a 1º alcohol) Ethanol (O from K2Cr2O7) ethanalethanoicacid • CH3-CH2-CH2OH+ CH3-COOHCH3-CH2-CH2-O-CO-CH3 (esterification reaction) propan-1-olethanoic acid propyl ethanoate

  3. Reaction pathways • Series of steps to convert one organic compound into a different organic product • Putting together a reaction pathway is a lot like doing a puzzle • Start with given materials and determine what the final product should be • Figure out how to use starting materials to create final product

  4. Summary of substitution reactions • Alkanes convert to halogenoalkanes via a substitution reaction • A Hydrogen in alkane replaced with halogen atom from a halogen molecule • Uses exposure to UV light • Halogenoalkanesconvert to alcohols via a nucleophilic substitution reaction • Halogen in the halogenoalkane is replaced with an OH group via an SN1 or SN2 mechanism

  5. Summary of Addition reactions • Alkenesconvert to alcohols via addition reaction • Water added across double bond in presence of an acid catalyst (like sulfuric acid) • Alkenesconvert to alkanes via addition reaction • Hydrogen gas added across double bond in presence of nickel catalyst • Alkenesconvert to halogenoalkanesvia addition reaction • Halogen added across double bond

  6. Summary of oxidation reactions • 1º alcohols convert to aldehydes via oxidation RXN • Acidified potassium dichromate (H+/K2Cr2O7) added to alcohol and heated • As aldehyde produced, removed via distillation • Aldehydesconvert to carboxylic acids via a 2ndoxd. • Aldehydes produced via oxidation of 1º alcohols can be “refluxed” with H+/K2Cr2O7to yield the carboxylic acid • 2ºalcohols convert to ketones via an oxidation reaction • H+/K2Cr2O7 added to alcohol and heated

  7. condensation and elimination reactions • Alcoholscombined with carboxylic acids to form esters via a condensation reaction • Water is removed in the presence of an acid catalyst • Halogenoalkanesconvert to alkenes via elimination reaction • Halogenoalkane added to a concentrated solution of hydroxide ions in ethanol at a high temperature

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