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Reactions of Hydrocarbons: Combustion

Reactions of Hydrocarbons: Combustion. 2 CH 3 CH 2 CH 2 CH 3 ( g ) + 13 O 2 ( g ) → 8 CO 2 ( g ) + 10 H 2 O( g ) CH 3 CH=CHCH 3 ( g ) + 6 O 2 ( g ) → 4 CO 2 ( g ) + 4 H 2 O( g ) 2 CH 3 C  CCH 3 ( g ) + 11 O 2 ( g ) → 8 CO 2 ( g ) + 6 H 2 O( g ) Anything that contains carbon and hydrogen

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Reactions of Hydrocarbons: Combustion

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  1. Reactions of Hydrocarbons: Combustion 2 CH3CH2CH2CH3(g) + 13 O2(g) → 8 CO2(g) + 10 H2O(g) CH3CH=CHCH3(g) + 6 O2(g) → 4 CO2(g) + 4 H2O(g) 2 CH3CCCH3(g) + 11 O2(g) → 8 CO2(g) + 6 H2O(g) Anything that contains carbon and hydrogen (and often other elements)

  2. Reactions of Alkanes: Substitution light CH3CH3 + Br2®CH3CH2Br + HBr light CH3CH2CH2CH3 + Br2 → many products

  3. Alkene/alkyne addition reactions • Hydrogenation: • addition of H2 (with metal catalyst: Pt, Pd, Ni) Pt CH2=CHCH3 + H2®CH3CH2CH3 Pd + H2® • Halogenation: addition of X2 (Cl2, Br2, I2) CH2=CHCH3+ Br2®CH2BrCHBrCH3

  4. Alkene/alkyne addition reactions, cont. • Hydrohalogenation(addition of HX, X = F, Cl, Br, or I) CH2=CHCH3+ HBr®CH3CHBrCH3 + 2HBr ® • Hydration (addition of H2O, or H + OH) H+ + H2O® • Markovnikov addition: “The rich get richer” • Carbon that starts with more hydrogens gets the additional hydrogen(s)

  5. Oxidation of alkenes In organic chemistry: Oxidation: carbon adds oxygen and/or loses hydrogen Reduction: carbon loses oxygen and/or adds hydrogen KMnO4 (aq) Cold, dilute also an addition reaction

  6. Oxidation of alkenes, cont. KMnO4 (aq) Hot, concentrated KMnO4 (aq) Hot, concentrated

  7. Reactions of aromatic compounds Substitution: Halogenation (with Cl2 or Br2 and Fe catalyst)

  8. Reactions of aromatic compounds, cont. • Oxidation • (of alkyl benzene at the first alkyl carbon)

  9. Reactions with Alcohols Elimination (backwards of addition) e.g. Dehydration • No reaction

  10. Reactions with Alcohols, cont. • Oxidation 1° alcohols  aldehydes, carboxylic acids 2° alcohols  ketones 3° alcohols  NO REACTION

  11. No reaction • Also note: • No reaction

  12. Reactions with Alcohols, cont. • Reduction (for 1°, 2° or 3°) 2 HO-R + 2 Na  2 NaOR + H2 (g) recall: 2 Na + 2 H2O  2 NaOH + H2 (g)

  13. Phenol as an acid + NaOH + H2O Strong base Weak acid Acid/base reaction

  14. Reactions of Aldehydes and Ketones Oxidation of aldehydes to carboxylic acids: RCHO RCOOH

  15. Reactions of Aldehydes and Ketones, cont. • Reductionof aldehydes and ketones to alcohols primary and secondary alcohols • Several possible catalysts, a few examples:

  16. Reactions of carboxylic acids Acid/base reactions: sodium acetate acetic acid • sodium pentanaote

  17. Reactions of carboxylic acids, cont. • Esterification:

  18. Amine Reactions Amines are weak organic bases. Will react with strong acids to form ammonium salts RNH2 + HCl → RNH3+Cl− (recall: NH3 + HCl → NH4+Cl− ) When they react with carboxylic acids in a condensation reaction, an amide is produced.

  19. Amine Reactions, cont. Amide formation from reaction of primary or secondary amines or ammonia with carboxylic acid: • 1° amine • 2° amide • ammonia • 1° amide

  20. Hydrolysis of esters and amides Water (with acid or base) breaks the ester and amide linkages.

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